# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_4
_database_code_depnum_ccdc_archive 'CCDC 1574946'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_1_4                 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystals supplied were small, very 
weakly diffracting and exhibited rapid fall-off, 
even with prolonged exposure times using 
synchrotron radiation. This is a common problem 
for supramolecular data collections. However, 
the identity of the structure was clearly 
established without issue. 
;
_vrf_PLAT112_1_4                 
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.        m        100 %Fit  
RESPONSE: All centrosymmetric space groups 
explored were unable to solve to a rational 
structure (including I4/mcm). The poor quality 
of the diffraction data, which required synchrotron 
radiation to collect, in combination with the 
Squeeze protocol in Platon being used to account 
for the extensive sphere of disordered solvates 
present, have erroneously indicated that a 
centrosymmetric space group should be selected. 
;
_vrf_PLAT113_1_4                 
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group     I4/mcm Check 
RESPONSE: All centrosymmetric space groups 
explored were unable to solve to a rational 
structure (including I4/mcm). The poor quality 
of the diffraction data, which required synchrotron 
radiation to collect, in combination with the 
Squeeze protocol in Platon being used to account 
for the extensive sphere of disordered solvates 
present, have erroneously indicated that a 
centrosymmetric space group should be selected. 
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H24 N4 Ni O8, C29 H32 N8'
_chemical_formula_sum            'C77 H56 N12 Ni O8'
_chemical_formula_weight         1336.04
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   17.556(3)
_cell_length_b                   17.556(3)
_cell_length_c                   56.930(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     17547(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      45.2
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.506
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.740
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            42023
_diffrn_reflns_point_group_measured_fraction_full 0.740
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         22.746
_diffrn_reflns_theta_min         0.715
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.740
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.976
_reflns_Friedel_fraction_full    0.739
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                7204
_reflns_number_total             11743
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.014
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.470(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         11743
_refine_ls_number_restraints     465
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1106
_refine_special_details          
'Refined as a 2-component inversion twin.,SQUEEZE'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.530(18)
 0.470(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
3. Restrained distances
 C53-C53_$1
 1.42 with sigma of 0.01
 C73_$1-C73
 1.42 with sigma of 0.01
 C72-C73
 1.42 with sigma of 0.01
 O89-C87 = O88-C87
 1.3 with sigma of 0.02
 N71-C72
 1.42 with sigma of 0.01
 C66-C65
 1.3 with sigma of 0.01
 C53-C52
 1.42 with sigma of 0.01
 N51-C52
 1.42 with sigma of 0.01
 C84-C87
 1.45 with sigma of 0.02
 C81-C56
 1.4 with sigma of 0.01
 C56-C52
 1.5 with sigma of 0.01
 C97-C94
 1.5 with sigma of 0.02
 O99-C97 = O98-C97
 1.3 with sigma of 0.02
 N12-C14
 2.3 with sigma of 0.01
 N11-N12
 2.05 with sigma of 0.02
 H11A-H12A
 2.1 with sigma of 0.01
 C72_$1-C72
 2.3 with sigma of 0.02
 C52_$1-C52
 2.3 with sigma of 0.02
 O88-C84
 2.4 with sigma of 0.02
 O89-C84
 2.4 with sigma of 0.02
4. Restrained planarity
 O88_$2, O89_$2, N11_$1, H11A_$1, H11B_$1, N12_$1, H12A_$1, H12B_$1, C87_$2,
 C13_$1
 with sigma of 0.1
 N71, C73, C73_$1, C72
 with sigma of 0.1
 N61_$1, C62_$1, C64_$1, C63_$1, C65_$1
 with sigma of 0.1
 N71, N61, C62, C64, C73, C73_$1, C63, C65, C66, C72, C72_$1
 with sigma of 0.1
 N51, C52_$1, C52, C53, C53_$1
 with sigma of 0.1
 O88, O89, C83, C87, C85, C81, C84, C82, C86
 with sigma of 0.1
 O98, O99, C93, C95, C97, C96, C92, C94, C91
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
Uanis(C13) = Uanis(N11) = Uanis(N12)
6. Rigid body (RIGU) restrains
 N1, H1A, H1B, N2, H2A, H2B, N11, H11A, H11B, N12, H12A, H12B, C5, H5, C4, C17,
  C16, H16, C9, H9, C3, C8, H8, C7, C6, H6, C10, C13, C15, H15, C14, C19, H19,
 C18, H18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Ni51, O88, O98, O99, O89, N71, N51, N61, C83, C93, C87, C85, C81, C95, C84,
 C97, C82, C86, C62, C96, C92, C94, C64, C73, C52, C63, C53, C65, C91, C66, C72,
  C56
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
7. Others
 Fixed Uiso: H63(0.2) H64(0.2) H85(0.2) H83(0.2) H82(0.2) H86(0.2) H96(0.2)
 H92(0.2) H93(0.2) H95(0.2) H73(0.2) H53(0.2)
 Fixed Z: Ni51(0.570889)
8.a Aromatic/amide H refined with riding coordinates:
 C63(H63), C64(H64), C5(H5), C9(H9), C8(H8), C6(H6), C85(H85), C83(H83),
 C82(H82), C86(H86), C96(H96), C92(H92), C93(H93), C95(H95), C15(H15), C19(H19),
  C18(H18), C16(H16), C73(H73), C53(H53)
8.b Fitted pentagon refined as free rotating group:
 N61(C62,C63,C64,C65)
8.c Fitted hexagon refined as free rotating group:
 C5(C4,C9,C8,C7,C6), C85(C84,C83,C82,C81,C86), C96(C91,C92,C93,C94,C95),
 C15(C14,C19,C18,C17,C16)
8.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N11(H11A,H11B), N12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni51 Ni 0.5000 1.0000 0.5709 0.1092(3) Uani 1 2 d S TU P . .
O88 O 0.7840(3) 0.8139(3) 0.70289(10) 0.224(3) Uani 1 1 d D U . . .
O98 O 0.7071(3) 0.6983(4) 0.43744(9) 0.271(4) Uani 1 1 d D U . . .
O99 O 0.8028(3) 0.7881(3) 0.43735(9) 0.256(3) Uani 1 1 d D U . . .
O89 O 0.6916(4) 0.7084(4) 0.70204(9) 0.248(3) Uani 1 1 d D U . . .
N71 N 0.5000 1.0000 0.53428(9) 0.148(3) Uani 1 2 d DS TU P . .
N1 N 0.7361(2) 0.8494(2) 0.89538(6) 0.1226(13) Uani 1 1 d . U . . .
H1A H 0.7604 0.8219 0.9059 0.147 Uiso 1 1 calc R U . . .
H1B H 0.7556 0.8928 0.8905 0.147 Uiso 1 1 calc R U . . .
N51 N 0.5000 1.0000 0.60324(7) 0.117(2) Uani 1 2 d DS TU P . .
N61 N 0.57857(19) 0.91955(18) 0.56935(7) 0.1628(17) Uani 1 1 d . U . . .
C62 C 0.6111(3) 0.8860(3) 0.58970(6) 0.177(3) Uani 1 1 d G U . . .
C63 C 0.6671(3) 0.8328(3) 0.58229(9) 0.237(5) Uani 1 1 d G U . . .
H63 H 0.6979 0.8022 0.5923 0.200 Uiso 1 1 calc R . . . .
C64 C 0.6692(3) 0.8335(3) 0.55736(9) 0.224(4) Uani 1 1 d G U . . .
H64 H 0.7015 0.8034 0.5477 0.200 Uiso 1 1 calc R . . . .
C65 C 0.6144(3) 0.8871(3) 0.54936(6) 0.174(3) Uani 1 1 d DG U . . .
N2 N 0.6488(2) 0.7608(2) 0.89564(6) 0.1248(13) Uani 1 1 d . U . . .
H2A H 0.6750 0.7351 0.9062 0.150 Uiso 1 1 calc R U . . .
H2B H 0.6051 0.7427 0.8904 0.150 Uiso 1 1 calc R U . . .
N11 N 0.6238(3) 1.2113(3) 0.73513(7) 0.1668(13) Uani 1 1 d D U . . .
H11A H 0.6295 1.2170 0.7199 0.200 Uiso 1 1 calc DR U . . .
H11B H 0.5901 1.2390 0.7427 0.200 Uiso 1 1 calc R U . . .
N12 N 0.7087(3) 1.1269(3) 0.73641(7) 0.1668(13) Uani 1 1 d D U . . .
H12A H 0.7164 1.1305 0.7212 0.200 Uiso 1 1 calc DR U . . .
H12B H 0.7354 1.0944 0.7448 0.200 Uiso 1 1 calc R U . . .
C5 C 0.56532(17) 0.84032(14) 0.86142(5) 0.1153(15) Uani 1 1 d . U . . .
H5 H 0.5487 0.7914 0.8664 0.138 Uiso 1 1 calc R U . . .
C4 C 0.62897(15) 0.87361(16) 0.87169(4) 0.0921(12) Uani 1 1 d G U . . .
C9 C 0.65324(14) 0.94514(17) 0.86437(5) 0.1210(16) Uani 1 1 d G U . . .
H9 H 0.6967 0.9679 0.8714 0.145 Uiso 1 1 calc R U . . .
C8 C 0.61387(16) 0.98337(14) 0.84677(5) 0.1142(15) Uani 1 1 d G U . . .
H8 H 0.6305 1.0323 0.8418 0.137 Uiso 1 1 calc R U . . .
C7 C 0.55023(14) 0.95008(14) 0.83649(4) 0.0753(10) Uani 1 1 d G U . . .
C6 C 0.52596(14) 0.87856(15) 0.84382(4) 0.1146(16) Uani 1 1 d G U . . .
H6 H 0.4825 0.8558 0.8368 0.138 Uiso 1 1 calc R U . . .
C87 C 0.7275(6) 0.7714(6) 0.69787(17) 0.233(5) Uani 1 1 d D U . . .
C85 C 0.6303(3) 0.7678(3) 0.66267(9) 0.223(4) Uani 1 1 d . U . . .
H85 H 0.6093 0.7226 0.6691 0.200 Uiso 1 1 calc R . . . .
C84 C 0.6910(3) 0.8038(3) 0.67378(7) 0.226(4) Uani 1 1 d DG U . . .
C83 C 0.7217(2) 0.8700(3) 0.66430(8) 0.209(4) Uani 1 1 d G U . . .
H83 H 0.7631 0.8945 0.6719 0.200 Uiso 1 1 calc R . . . .
C82 C 0.6917(3) 0.9002(2) 0.64371(8) 0.200(3) Uani 1 1 d G U . . .
H82 H 0.7127 0.9454 0.6372 0.200 Uiso 1 1 calc R . . . .
C81 C 0.6311(3) 0.8642(3) 0.63260(6) 0.187(3) Uani 1 1 d DG U . . .
C86 C 0.6004(3) 0.7980(3) 0.64208(8) 0.232(4) Uani 1 1 d G U . . .
H86 H 0.5589 0.7735 0.6345 0.200 Uiso 1 1 calc R . . . .
C3 C 0.6753(3) 0.8273(3) 0.88751(6) 0.1095(14) Uani 1 1 d . U . . .
C97 C 0.7444(6) 0.7567(6) 0.44655(16) 0.261(6) Uani 1 1 d D U . . .
C96 C 0.7125(3) 0.8920(2) 0.49978(8) 0.187(3) Uani 1 1 d . U . . .
H96 H 0.7353 0.9354 0.5068 0.200 Uiso 1 1 calc R . . . .
C91 C 0.6460(3) 0.8616(3) 0.50918(6) 0.176(3) Uani 1 1 d G U . . .
C92 C 0.6126(2) 0.7981(3) 0.49888(8) 0.201(3) Uani 1 1 d G U . . .
H92 H 0.5672 0.7773 0.5053 0.200 Uiso 1 1 calc R . . . .
C93 C 0.6456(3) 0.7650(2) 0.47917(8) 0.208(3) Uani 1 1 d G U . . .
H93 H 0.6227 0.7216 0.4721 0.200 Uiso 1 1 calc R . . . .
C94 C 0.7120(3) 0.7954(3) 0.46977(7) 0.196(3) Uani 1 1 d DG U . . .
C95 C 0.7455(2) 0.8589(3) 0.48007(8) 0.200(3) Uani 1 1 d G U . . .
H95 H 0.7909 0.8797 0.4736 0.200 Uiso 1 1 calc R . . . .
C10 C 0.5000 1.0000 0.81956(9) 0.0691(10) Uani 1 2 d S TU P . .
C13 C 0.6623(4) 1.1658(4) 0.74560(10) 0.1668(13) Uani 1 1 d . U . . .
C15 C 0.64816(16) 1.0513(2) 0.77394(6) 0.1247(17) Uani 1 1 d . U . . .
H15 H 0.6904 1.0279 0.7664 0.150 Uiso 1 1 calc R U . . .
C14 C 0.62597(19) 1.1244(2) 0.76747(6) 0.1324(18) Uani 1 1 d DG U . . .
C19 C 0.5641(2) 1.15873(16) 0.77844(6) 0.146(2) Uani 1 1 d G U . . .
H19 H 0.5490 1.2087 0.7740 0.175 Uiso 1 1 calc R U . . .
C18 C 0.52449(16) 1.12002(17) 0.79588(5) 0.1239(18) Uani 1 1 d G U . . .
H18 H 0.4822 1.1435 0.8034 0.149 Uiso 1 1 calc R U . . .
C17 C 0.54668(15) 1.04697(15) 0.80235(4) 0.0775(10) Uani 1 1 d G U . . .
C16 C 0.60851(17) 1.01263(14) 0.79138(5) 0.1244(17) Uani 1 1 d G U . . .
H16 H 0.6237 0.9627 0.7958 0.149 Uiso 1 1 calc R U . . .
C73 C 0.5313(4) 0.9755(4) 0.49631(8) 0.212(4) Uani 1 1 d D U . . .
H73 H 0.5578 0.9575 0.4828 0.200 Uiso 1 1 calc R . . . .
C52 C 0.5415(4) 0.9513(4) 0.61869(8) 0.198(4) Uani 1 1 d D U . . .
C53 C 0.5240(4) 0.9697(4) 0.64278(8) 0.170(3) Uani 1 1 d D U . . .
H53 H 0.5428 0.9441 0.6563 0.200 Uiso 1 1 calc R . . . .
C66 C 0.5983(4) 0.9076(4) 0.52844(9) 0.166(3) Uani 1 1 d D U . . .
C72 C 0.5485(4) 0.9573(4) 0.52013(8) 0.199(4) Uani 1 1 d D U . . .
C56 C 0.5960(4) 0.8902(4) 0.61142(10) 0.189(3) Uani 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni51 N71 2.084(5) . ?
Ni51 N51 1.842(4) . ?
Ni51 N61 1.976(2) 2_675 ?
Ni51 N61 1.976(2) . ?
O88 C87 1.272(11) . ?
O98 C97 1.323(9) . ?
O99 C97 1.276(9) . ?
O89 C87 1.296(11) . ?
N71 C72 1.391(6) . ?
N71 C72 1.391(6) 2_675 ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C3 1.222(5) . ?
N51 C52 1.427(5) . ?
N51 C52 1.427(5) 2_675 ?
N61 C62 1.4200 . ?
N61 C65 1.4200 . ?
C62 C63 1.4200 . ?
C62 C56 1.267(6) . ?
C63 H63 0.9500 . ?
C63 C64 1.4200 . ?
C64 H64 0.9500 . ?
C64 C65 1.4200 . ?
C65 C66 1.276(6) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C3 1.340(5) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C13 1.204(6) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N12 C13 1.184(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C5 C6 1.3900 . ?
C4 C9 1.3900 . ?
C4 C3 1.460(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.3900 . ?
C8 H8 0.9500 . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C7 C10 1.573(4) . ?
C6 H6 0.9500 . ?
C87 C84 1.617(9) . ?
C85 H85 0.9500 . ?
C85 C84 1.3900 . ?
C85 C86 1.3900 . ?
C84 C83 1.3900 . ?
C83 H83 0.9500 . ?
C83 C82 1.3900 . ?
C82 H82 0.9500 . ?
C82 C81 1.3900 . ?
C81 C86 1.3900 . ?
C81 C56 1.428(6) . ?
C86 H86 0.9500 . ?
C97 C94 1.591(8) . ?
C96 H96 0.9500 . ?
C96 C91 1.3900 . ?
C96 C95 1.3900 . ?
C91 C92 1.3900 . ?
C91 C66 1.599(6) . ?
C92 H92 0.9500 . ?
C92 C93 1.3900 . ?
C93 H93 0.9500 . ?
C93 C94 1.3900 . ?
C94 C95 1.3900 . ?
C95 H95 0.9500 . ?
C10 C7 1.573(4) 2_675 ?
C10 C17 1.520(5) 2_675 ?
C10 C17 1.521(4) . ?
C13 C14 1.576(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.3900 . ?
C15 C16 1.3900 . ?
C14 C19 1.3900 . ?
C19 H19 0.9500 . ?
C19 C18 1.3900 . ?
C18 H18 0.9500 . ?
C18 C17 1.3900 . ?
C17 C16 1.3900 . ?
C16 H16 0.9500 . ?
C73 C73 1.396(9) 2_675 ?
C73 H73 0.9500 . ?
C73 C72 1.425(6) . ?
C52 C53 1.442(6) . ?
C52 C56 1.495(7) . ?
C53 C53 1.356(9) 2_675 ?
C53 H53 0.9500 . ?
C66 C72 1.323(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N51 Ni51 N71 180.0 . . ?
N51 Ni51 N61 92.54(12) . . ?
N51 Ni51 N61 92.54(12) . 2_675 ?
N61 Ni51 N71 87.46(12) 2_675 . ?
N61 Ni51 N71 87.46(12) . . ?
N61 Ni51 N61 174.9(2) 2_675 . ?
C72 N71 Ni51 125.4(3) 2_675 . ?
C72 N71 Ni51 125.4(3) . . ?
C72 N71 C72 109.2(6) 2_675 . ?
H1A N1 H1B 120.0 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
C52 N51 Ni51 128.0(3) . . ?
C52 N51 Ni51 128.0(3) 2_675 . ?
C52 N51 C52 103.9(5) 2_675 . ?
C62 N61 Ni51 122.8(3) . . ?
C65 N61 Ni51 129.2(3) . . ?
C65 N61 C62 108.0 . . ?
N61 C62 C63 108.0 . . ?
C56 C62 N61 133.5(4) . . ?
C56 C62 C63 118.2(4) . . ?
C62 C63 H63 126.0 . . ?
C64 C63 C62 108.0 . . ?
C64 C63 H63 126.0 . . ?
C63 C64 H64 126.0 . . ?
C63 C64 C65 108.0 . . ?
C65 C64 H64 126.0 . . ?
N61 C65 C64 108.0 . . ?
C66 C65 N61 122.4(4) . . ?
C66 C65 C64 129.5(4) . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C13 N11 H11A 120.0 . . ?
C13 N11 H11B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C13 N12 H12A 120.0 . . ?
C13 N12 H12B 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C4 C3 118.2(3) . . ?
C9 C4 C5 120.0 . . ?
C9 C4 C3 121.2(3) . . ?
C4 C9 H9 120.0 . . ?
C4 C9 C8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 C10 118.31(16) . . ?
C6 C7 C10 121.01(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
O88 C87 O89 147.0(9) . . ?
O88 C87 C84 107.1(8) . . ?
O89 C87 C84 105.2(8) . . ?
C84 C85 H85 120.0 . . ?
C84 C85 C86 120.0 . . ?
C86 C85 H85 120.0 . . ?
C85 C84 C87 122.0(6) . . ?
C83 C84 C87 117.9(6) . . ?
C83 C84 C85 120.0 . . ?
C84 C83 H83 120.0 . . ?
C84 C83 C82 120.0 . . ?
C82 C83 H83 120.0 . . ?
C83 C82 H82 120.0 . . ?
C81 C82 C83 120.0 . . ?
C81 C82 H82 120.0 . . ?
C82 C81 C86 120.0 . . ?
C82 C81 C56 124.7(5) . . ?
C86 C81 C56 115.3(5) . . ?
C85 C86 H86 120.0 . . ?
C81 C86 C85 120.0 . . ?
C81 C86 H86 120.0 . . ?
N1 C3 N2 117.0(4) . . ?
N1 C3 C4 122.4(5) . . ?
N2 C3 C4 120.4(5) . . ?
O98 C97 C94 118.7(8) . . ?
O99 C97 O98 124.8(7) . . ?
O99 C97 C94 116.3(7) . . ?
C91 C96 H96 120.0 . . ?
C91 C96 C95 120.0 . . ?
C95 C96 H96 120.0 . . ?
C96 C91 C66 120.7(4) . . ?
C92 C91 C96 120.0 . . ?
C92 C91 C66 118.2(4) . . ?
C91 C92 H92 120.0 . . ?
C91 C92 C93 120.0 . . ?
C93 C92 H92 120.0 . . ?
C92 C93 H93 120.0 . . ?
C94 C93 C92 120.0 . . ?
C94 C93 H93 120.0 . . ?
C93 C94 C97 117.1(5) . . ?
C93 C94 C95 120.0 . . ?
C95 C94 C97 122.8(5) . . ?
C96 C95 H95 120.0 . . ?
C94 C95 C96 120.0 . . ?
C94 C95 H95 120.0 . . ?
C7 C10 C7 104.4(4) . 2_675 ?
C17 C10 C7 113.26(15) . . ?
C17 C10 C7 113.3(3) 2_675 . ?
C17 C10 C7 113.3(3) 2_675 2_675 ?
C17 C10 C7 113.3(2) . 2_675 ?
C17 C10 C17 99.7(5) 2_675 . ?
N11 C13 C14 118.1(5) . . ?
N12 C13 N11 123.3(5) . . ?
N12 C13 C14 111.2(5) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 C19 120.0 . . ?
C19 C14 C13 118.1(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 C10 121.34(18) . . ?
C16 C17 C10 118.38(18) . . ?
C16 C17 C18 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C73 C73 H73 126.1 2_675 . ?
C73 C73 C72 107.7(3) 2_675 . ?
C72 C73 H73 126.1 . . ?
N51 C52 C53 110.0(5) . . ?
N51 C52 C56 125.9(4) . . ?
C53 C52 C56 124.1(4) . . ?
C52 C53 H53 126.0 . . ?
C53 C53 C52 108.0(3) 2_675 . ?
C53 C53 H53 126.0 2_675 . ?
C65 C66 C91 112.4(5) . . ?
C65 C66 C72 131.8(5) . . ?
C72 C66 C91 115.7(4) . . ?
N71 C72 C73 107.5(5) . . ?
C66 C72 N71 123.6(4) . . ?
C66 C72 C73 128.9(5) . . ?
C62 C56 C81 135.7(6) . . ?
C62 C56 C52 116.4(5) . . ?
C81 C56 C52 105.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.530(18)
2 0.470(18)
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3_4
_database_code_depnum_ccdc_archive 'CCDC 1574948'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;
#==============================================================================
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.004 0.250 0.250 365 78 ' '
2 -0.053 0.250 0.750 365 78 ' '
3 -0.014 0.750 0.750 365 78 ' '
4 -0.004 0.750 0.250 365 78 ' '
_platon_squeeze_details          
;
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
;The asymmetric unit cell contains one half of the porphyrin molecule,
one bis-amidinium molecule, one water molecule, and a region of diffuse
electron density that appears to arise from disordered solvent molecules.
This could not be modelled sensibly and so PLATON-SQUEEZE was used to include
this electron density in the refinement.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H and O-H hydrogen 
atoms were inserted at calculated positions and were refined with restraints 
on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement.,SQUEEZE
;

_cell_length_a                   10.86990(10)
_cell_length_b                   24.1347(2)
_cell_length_c                   24.7076(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6481.84(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n a '
_symmetry_space_group_name_Hall  '-P 2a 2bc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2
-x+1/2,-y,z
x+1/2,y,-z
x,-y+1/2,-z+1/2
-x,y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ni -3.0029 0.5091 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

_chemical_formula_sum            'C64 H52 N12 Ni1 O10'
_chemical_formula_moiety         'C48 H24 N4 Ni O8, 2(C8 H12 N4), 2 (H2 O)'
_chemical_compound_source        synthesized
_chemical_formula_weight         1207.90

_cell_measurement_reflns_used    31637
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      73.6
_cell_measurement_temperature    150

_exptl_crystal_description       rod
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_max          0.41

_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2512
_exptl_absorpt_coefficient_mu    0.967

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            104624
_reflns_number_total             6567
_diffrn_reflns_av_R_equivalents  0.043

_diffrn_reflns_theta_min         2.559
_diffrn_reflns_theta_max         74.007
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        74.007
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              0
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              29
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   1.85
_oxford_diffrn_Wilson_scale      0.21

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.09
_refine_diff_density_max         1.79

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         6541
_refine_ls_number_restraints     18
_refine_ls_number_parameters     427
_oxford_refine_ls_R_factor_ref   0.0762
_refine_ls_wR_factor_ref         0.2099
_refine_ls_goodness_of_fit_ref   1.0690
_refine_ls_shift/su_max          0.0007745
_refine_ls_shift/su_mean         0.0000711

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6541
_refine_ls_R_factor_all          0.0762
_refine_ls_wR_factor_all         0.2099

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5971
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_gt          0.2069

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.363E+04 0.617E+04 0.386E+04 0.163E+04 364. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.7287(2) 1.04465(10) 0.85204(7) 0.0459 1.0000 Uani . . . . . .
C2 C 0.7500 1.0000 0.82920(15) 0.0361 1.0000 Uani S T . . . .
C3 C 0.7500 1.0000 0.76708(13) 0.0311 1.0000 Uani S T . . . .
C4 C 0.7627(3) 1.04917(12) 0.73828(10) 0.0418 1.0000 Uani . . . . . .
C5 C 0.7632(3) 1.04931(11) 0.68217(10) 0.0371 1.0000 Uani . . . . . .
C6 C 0.7500 1.0000 0.65289(13) 0.0246 1.0000 Uani S T . . . .
C7 C 0.7500 1.0000 0.59217(12) 0.0216 1.0000 Uani S T . . . .
C8 C 0.6564(2) 1.02728(8) 0.56487(7) 0.0203 1.0000 Uani . . . . . .
N9 N 0.65544(16) 1.03741(6) 0.50952(6) 0.0167 1.0000 Uani . . . . . .
C10 C 0.56311(18) 1.07604(7) 0.50211(7) 0.0184 1.0000 Uani . . . . . .
C11 C 0.5571(2) 1.05567(9) 0.59076(8) 0.0262 1.0000 Uani . . . . . .
C12 C 0.5010(2) 1.08688(9) 0.55234(8) 0.0258 1.0000 Uani . . . . . .
C13 C 0.53686(19) 1.10346(8) 0.45454(7) 0.0169 1.0000 Uani . . . . . .
C14 C 0.58767(18) 1.08734(8) 0.40549(7) 0.0183 1.0000 Uani . . . . . .
N15 N 0.66708(16) 1.04319(6) 0.39816(6) 0.0164 1.0000 Uani . . . . . .
C16 C 0.68132(19) 1.03972(8) 0.34278(7) 0.0193 1.0000 Uani . . . . . .
C17 C 0.5562(2) 1.11225(9) 0.35497(8) 0.0268 1.0000 Uani . . . . . .
C18 C 0.6134(2) 1.08261(9) 0.31610(8) 0.0261 1.0000 Uani . . . . . .
C19 C 0.7500 1.0000 0.31555(12) 0.0186 1.0000 Uani S T . . . .
C20 C 0.7500 1.0000 0.25542(12) 0.0203 1.0000 Uani S T . . . .
C21 C 0.64212(19) 0.98796(9) 0.22675(8) 0.0231 1.0000 Uani . . . . . .
C22 C 0.64225(19) 0.98772(9) 0.17061(8) 0.0216 1.0000 Uani . . . . . .
C23 C 0.7500 1.0000 0.14200(11) 0.0153 1.0000 Uani S T . . . .
C24 C 0.7500 1.0000 0.08111(12) 0.0197 1.0000 Uani S T . . . .
O25 O 0.65639(14) 0.98167(7) 0.05755(6) 0.0263 1.0000 Uani . . . . . .
C26 C 0.45337(18) 1.15277(8) 0.45542(7) 0.0172 1.0000 Uani . . . . . .
C27 C 0.49861(18) 1.20451(8) 0.47023(9) 0.0211 1.0000 Uani . . . . . .
C28 C 0.42234(17) 1.25084(8) 0.47039(8) 0.0199 1.0000 Uani . . . . . .
C29 C 0.29989(17) 1.24634(8) 0.45427(7) 0.0171 1.0000 Uani . . . . . .
C30 C 0.25557(17) 1.19508(10) 0.43844(10) 0.0231 1.0000 Uani . . . . . .
C31 C 0.33032(19) 1.14862(9) 0.43956(9) 0.0240 1.0000 Uani . . . . . .
C32 C 0.21607(19) 1.29656(8) 0.45392(8) 0.0192 1.0000 Uani . . . . . .
O33 O 0.23855(14) 1.33527(6) 0.48595(7) 0.0280 1.0000 Uani . . . . . .
O34 O 0.12650(13) 1.29490(7) 0.42165(7) 0.0291 1.0000 Uani . . . . . .
N51 N 0.61434(18) 0.67153(12) 0.32172(9) 0.0405 1.0000 Uani D . . . . .
N52 N 0.61576(15) 0.66605(9) 0.41420(8) 0.0274 1.0000 Uani D . . . . .
C53 C 0.67235(19) 0.66429(9) 0.36754(10) 0.0276 1.0000 Uani D . . . . .
N54 N 0.97625(17) 0.58579(7) 0.50478(7) 0.0220 1.0000 Uani D . . . . .
N55 N 1.12904(16) 0.54991(8) 0.45179(7) 0.0214 1.0000 Uani D . . . . .
C56 C 1.03132(18) 0.58111(8) 0.45742(8) 0.0190 1.0000 Uani D . . . . .
C57 C 0.80745(19) 0.65415(9) 0.36730(9) 0.0245 1.0000 Uani . . . . . .
C58 C 0.85611(18) 0.62292(8) 0.40888(8) 0.0201 1.0000 Uani . . . . . .
C59 C 0.98209(18) 0.61257(8) 0.41109(8) 0.0194 1.0000 Uani . . . . . .
C60 C 1.0576(2) 0.63350(11) 0.37072(10) 0.0348 1.0000 Uani . . . . . .
C61 C 1.0091(2) 0.66463(15) 0.32904(11) 0.0473 1.0000 Uani . . . . . .
C62 C 0.8836(2) 0.67573(13) 0.32723(10) 0.0387 1.0000 Uani . . . . . .
O101 O 0.85539(19) 0.65105(13) 0.67581(8) 0.0544 1.0000 Uani D . . . . .
Ni1 Ni 0.7500 1.0000 0.453827(17) 0.0130 1.0000 Uani S T . . . .
H41 H 0.7719 1.0839 0.7571 0.0485 1.0000 Uiso R . . . . .
H51 H 0.7726 1.0842 0.6633 0.0443 1.0000 Uiso R . . . . .
H111 H 0.5368 1.0524 0.6282 0.0311 1.0000 Uiso R . . . . .
H121 H 0.4333 1.1113 0.5569 0.0305 1.0000 Uiso R . . . . .
H171 H 0.5042 1.1437 0.3502 0.0327 1.0000 Uiso R . . . . .
H181 H 0.6111 1.0885 0.2781 0.0305 1.0000 Uiso R . . . . .
H211 H 0.5677 0.9802 0.2461 0.0282 1.0000 Uiso R . . . . .
H221 H 0.5683 0.9790 0.1519 0.0254 1.0000 Uiso R . . . . .
H271 H 0.5818 1.2083 0.4807 0.0266 1.0000 Uiso R . . . . .
H281 H 0.4537 1.2855 0.4815 0.0253 1.0000 Uiso R . . . . .
H301 H 0.1724 1.1915 0.4272 0.0277 1.0000 Uiso R . . . . .
H311 H 0.2973 1.1124 0.4308 0.0299 1.0000 Uiso R . . . . .
H581 H 0.8024 0.6072 0.4355 0.0230 1.0000 Uiso R . . . . .
H601 H 1.1440 0.6255 0.3721 0.0409 1.0000 Uiso R . . . . .
H611 H 1.0607 0.6792 0.3009 0.0568 1.0000 Uiso R . . . . .
H621 H 0.8497 0.6980 0.2990 0.0473 1.0000 Uiso R . . . . .
H552 H 1.166(2) 0.5466(11) 0.4227(8) 0.0271 1.0000 Uiso D . . . . .
H541 H 0.916(2) 0.6081(10) 0.5105(8) 0.0283 1.0000 Uiso D . . . . .
H522 H 0.657(2) 0.6630(13) 0.4447(7) 0.0355 1.0000 Uiso D . . . . .
H551 H 1.159(2) 0.5336(10) 0.4794(8) 0.0276 1.0000 Uiso D . . . . .
H542 H 1.007(2) 0.5682(10) 0.5343(8) 0.0283 1.0000 Uiso D . . . . .
H512 H 0.650(2) 0.6641(14) 0.2898(8) 0.0531 1.0000 Uiso D . . . . .
H521 H 0.5374(17) 0.6752(12) 0.4168(9) 0.0352 1.0000 Uiso D . . . . .
H1012 H 0.888(5) 0.6224(15) 0.660(2) 0.0933 1.0000 Uiso D . . . . .
H1011 H 0.850(5) 0.666(2) 0.6446(12) 0.0931 1.0000 Uiso D . . . . .
H511 H 0.5345(18) 0.6800(16) 0.3218(9) 0.0530 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.780(17)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.238(3) yes
C2 . C3 . 1.535(5) yes
C3 . C4 5_675 1.391(3) yes
C3 . C4 . 1.391(3) yes
C4 . C5 . 1.386(3) yes
C4 . H41 . 0.963 no
C5 . C6 . 1.400(3) yes
C5 . H51 . 0.968 no
C6 . C7 . 1.500(4) yes
C7 . C8 5_675 1.387(3) yes
C7 . C8 . 1.387(3) yes
C8 . N9 . 1.389(2) yes
C8 . C11 . 1.429(3) yes
N9 . C10 . 1.382(2) yes
N9 . Ni1 . 1.9404(16) yes
C10 . C12 . 1.437(3) yes
C10 . C13 . 1.379(3) yes
C11 . C12 . 1.357(3) yes
C11 . H111 . 0.955 no
C12 . H121 . 0.950 no
C13 . C14 . 1.387(2) yes
C13 . C26 . 1.497(2) yes
C14 . N15 . 1.383(2) yes
C14 . C17 . 1.427(3) yes
N15 . C16 . 1.380(2) yes
N15 . Ni1 . 1.9469(16) yes
C16 . C18 . 1.432(3) yes
C16 . C19 . 1.389(2) yes
C17 . C18 . 1.349(3) yes
C17 . H171 . 0.955 no
C18 . H181 . 0.950 no
C19 . C20 . 1.486(4) yes
C20 . C21 5_675 1.400(3) yes
C20 . C21 . 1.400(3) yes
C21 . C22 . 1.387(3) yes
C21 . H211 . 0.958 no
C22 . C23 . 1.400(2) yes
C22 . H221 . 0.951 no
C23 . C24 . 1.504(4) yes
C24 . O25 5_675 1.253(2) yes
C24 . O25 . 1.253(2) yes
C26 . C27 . 1.391(3) yes
C26 . C31 . 1.397(3) yes
C27 . C28 . 1.392(2) yes
C27 . H271 . 0.945 no
C28 . C29 . 1.394(3) yes
C28 . H281 . 0.944 no
C29 . C30 . 1.384(3) yes
C29 . C32 . 1.516(2) yes
C30 . C31 . 1.385(3) yes
C30 . H301 . 0.950 no
C31 . H311 . 0.969 no
C32 . O33 . 1.248(3) yes
C32 . O34 . 1.259(3) yes
N51 . C53 . 1.307(3) yes
N51 . H512 . 0.896(18) no
N51 . H511 . 0.892(18) no
N52 . C53 . 1.307(3) yes
N52 . H522 . 0.878(17) no
N52 . H521 . 0.882(17) no
C53 . C57 . 1.489(3) yes
N54 . C56 . 1.319(3) yes
N54 . H541 . 0.863(17) no
N54 . H542 . 0.909(17) no
N55 . C56 . 1.309(3) yes
N55 . H552 . 0.825(17) no
N55 . H551 . 0.853(17) no
C56 . C59 . 1.474(3) yes
C57 . C58 . 1.380(3) yes
C57 . C62 . 1.392(3) yes
C58 . C59 . 1.393(3) yes
C58 . H581 . 0.958 no
C59 . C60 . 1.387(3) yes
C60 . C61 . 1.379(3) yes
C60 . H601 . 0.959 no
C61 . C62 . 1.391(3) yes
C61 . H611 . 0.960 no
C62 . H621 . 0.956 no
O101 . H1012 . 0.873(19) no
O101 . H1011 . 0.855(19) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 5_675 C2 . O1 . 125.8(3) yes
O1 5_675 C2 . C3 . 117.11(17) yes
O1 . C2 . C3 . 117.11(17) yes
C2 . C3 . C4 5_675 120.78(15) yes
C2 . C3 . C4 . 120.78(15) yes
C4 5_675 C3 . C4 . 118.4(3) yes
C3 . C4 . C5 . 121.0(3) yes
C3 . C4 . H41 . 120.4 no
C5 . C4 . H41 . 118.6 no
C4 . C5 . C6 . 120.9(3) yes
C4 . C5 . H51 . 118.9 no
C6 . C5 . H51 . 120.2 no
C5 . C6 . C5 5_675 117.8(3) yes
C5 . C6 . C7 . 121.11(16) yes
C5 5_675 C6 . C7 . 121.11(16) yes
C6 . C7 . C8 5_675 119.10(13) yes
C6 . C7 . C8 . 119.10(13) yes
C8 5_675 C7 . C8 . 121.8(3) yes
C7 . C8 . N9 . 124.58(19) yes
C7 . C8 . C11 . 124.3(2) yes
N9 . C8 . C11 . 110.53(17) yes
C8 . N9 . C10 . 104.73(15) yes
C8 . N9 . Ni1 . 127.76(13) yes
C10 . N9 . Ni1 . 127.21(12) yes
N9 . C10 . C12 . 110.48(17) yes
N9 . C10 . C13 . 125.94(17) yes
C12 . C10 . C13 . 123.48(18) yes
C8 . C11 . C12 . 107.01(17) yes
C8 . C11 . H111 . 124.6 no
C12 . C11 . H111 . 128.3 no
C10 . C12 . C11 . 106.96(19) yes
C10 . C12 . H121 . 125.5 no
C11 . C12 . H121 . 127.6 no
C10 . C13 . C14 . 121.85(18) yes
C10 . C13 . C26 . 119.64(15) yes
C14 . C13 . C26 . 118.50(16) yes
C13 . C14 . N15 . 125.36(17) yes
C13 . C14 . C17 . 123.41(18) yes
N15 . C14 . C17 . 111.07(16) yes
C14 . N15 . C16 . 104.27(15) yes
C14 . N15 . Ni1 . 127.51(12) yes
C16 . N15 . Ni1 . 128.04(13) yes
N15 . C16 . C18 . 110.77(16) yes
N15 . C16 . C19 . 125.64(19) yes
C18 . C16 . C19 . 123.59(19) yes
C14 . C17 . C18 . 106.80(17) yes
C14 . C17 . H171 . 125.9 no
C18 . C17 . H171 . 127.3 no
C16 . C18 . C17 . 107.05(17) yes
C16 . C18 . H181 . 125.2 no
C17 . C18 . H181 . 127.7 no
C16 . C19 . C16 5_675 122.1(3) yes
C16 . C19 . C20 . 118.97(13) yes
C16 5_675 C19 . C20 . 118.97(13) yes
C19 . C20 . C21 5_675 120.38(13) yes
C19 . C20 . C21 . 120.38(13) yes
C21 5_675 C20 . C21 . 119.2(3) yes
C20 . C21 . C22 . 120.4(2) yes
C20 . C21 . H211 . 119.7 no
C22 . C21 . H211 . 119.9 no
C21 . C22 . C23 . 120.3(2) yes
C21 . C22 . H221 . 119.1 no
C23 . C22 . H221 . 120.5 no
C22 . C23 . C22 5_675 119.3(3) yes
C22 . C23 . C24 . 120.33(13) yes
C22 5_675 C23 . C24 . 120.33(13) yes
C23 . C24 . O25 5_675 117.68(14) yes
C23 . C24 . O25 . 117.68(14) yes
O25 5_675 C24 . O25 . 124.6(3) yes
C13 . C26 . C27 . 120.22(18) yes
C13 . C26 . C31 . 121.28(18) yes
C27 . C26 . C31 . 118.46(17) yes
C26 . C27 . C28 . 120.75(18) yes
C26 . C27 . H271 . 119.8 no
C28 . C27 . H271 . 119.4 no
C27 . C28 . C29 . 120.36(17) yes
C27 . C28 . H281 . 119.9 no
C29 . C28 . H281 . 119.8 no
C28 . C29 . C30 . 118.87(17) yes
C28 . C29 . C32 . 120.88(17) yes
C30 . C29 . C32 . 120.25(18) yes
C29 . C30 . C31 . 120.92(18) yes
C29 . C30 . H301 . 119.6 no
C31 . C30 . H301 . 119.4 no
C26 . C31 . C30 . 120.60(19) yes
C26 . C31 . H311 . 118.8 no
C30 . C31 . H311 . 120.5 no
C29 . C32 . O33 . 118.49(18) yes
C29 . C32 . O34 . 116.28(17) yes
O33 . C32 . O34 . 125.21(18) yes
C53 . N51 . H512 . 121.8(15) no
C53 . N51 . H511 . 119.9(15) no
H512 . N51 . H511 . 118(2) no
C53 . N52 . H522 . 121.0(14) no
C53 . N52 . H521 . 121.9(14) no
H522 . N52 . H521 . 116.5(20) no
N51 . C53 . N52 . 122.2(2) yes
N51 . C53 . C57 . 119.6(2) yes
N52 . C53 . C57 . 118.22(19) yes
C56 . N54 . H541 . 123.1(14) no
C56 . N54 . H542 . 120.1(13) no
H541 . N54 . H542 . 116.4(19) no
C56 . N55 . H552 . 122.6(14) no
C56 . N55 . H551 . 119.5(14) no
H552 . N55 . H551 . 118(2) no
N54 . C56 . N55 . 120.76(18) yes
N54 . C56 . C59 . 118.69(17) yes
N55 . C56 . C59 . 120.55(17) yes
C53 . C57 . C58 . 117.71(19) yes
C53 . C57 . C62 . 121.9(2) yes
C58 . C57 . C62 . 120.42(19) yes
C57 . C58 . C59 . 120.26(19) yes
C57 . C58 . H581 . 119.6 no
C59 . C58 . H581 . 120.1 no
C56 . C59 . C58 . 118.66(18) yes
C56 . C59 . C60 . 122.08(18) yes
C58 . C59 . C60 . 119.23(19) yes
C59 . C60 . C61 . 120.6(2) yes
C59 . C60 . H601 . 118.6 no
C61 . C60 . H601 . 120.8 no
C60 . C61 . C62 . 120.2(2) yes
C60 . C61 . H611 . 121.1 no
C62 . C61 . H611 . 118.6 no
C57 . C62 . C61 . 119.2(2) yes
C57 . C62 . H621 . 120.1 no
C61 . C62 . H621 . 120.7 no
H1012 . O101 . H1011 . 88(4) no
N15 5_675 Ni1 . N15 . 90.11(9) yes
N15 5_675 Ni1 . N9 5_675 90.38(7) yes
N15 . Ni1 . N9 5_675 174.45(7) yes
N15 5_675 Ni1 . N9 . 174.45(7) yes
N15 . Ni1 . N9 . 90.38(7) yes
N9 5_675 Ni1 . N9 . 89.67(9) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C31 . H311 . C8 6_456 159.04(6) 0.969 2.566 3.488(3) yes
C60 . H601 . O1 8_744 135.08(8) 0.959 2.443 3.195(3) yes
N55 . H552 . O1 8_744 174(3) 0.825 2.091 2.913(3) yes
N54 . H541 . O33 2_676 172.8(19) 0.863 2.164 3.022(3) yes
N52 . H522 . O33 2_676 173(3) 0.878 2.058 2.932(3) yes
N55 . H551 . O25 3_565 149.9(19) 0.853 1.966 2.738(3) yes
N54 . H542 . O25 3_565 140.9(18) 0.909 2.098 2.861(3) yes
N52 . H521 . O34 5_575 172(3) 0.882 1.926 2.803(3) yes
O101 . H1011 . O34 2_676 168(5) 0.855 1.904 2.746(3) yes
N51 . H511 . O101 6_456 147(3) 0.892 2.069 2.859(3) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 23/09/16 at  9:20:41
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL NI   (    1 ) 
CONT H    (  552 ,X'S)  UNTIL H    (  511 ) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
END      
;

_iucr_refine_instructions_details_restraints 
;                                                                  
#
# Punched on 23/09/16 at  9:20:41
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 51) TO H(512) 
CONT N ( 51) TO H(511) 
REST 0.052, 0.002 = H(512,U[ISO]) 
REST 0.052, 0.002 = H(511,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(53) TO N ( 51) TO H(512) 
CONT C(53) TO N ( 51) TO H(511) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 52) TO H(522) 
CONT N ( 52) TO H(521) 
REST 0.034, 0.002 = H(522,U[ISO]) 
REST 0.034, 0.002 = H(521,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(53) TO N ( 52) TO H(522) 
CONT C(53) TO N ( 52) TO H(521) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 54) TO H(541) 
CONT N ( 54) TO H(542) 
REST 0.027, 0.002 = H(541,U[ISO]) 
REST 0.027, 0.002 = H(542,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(56) TO N ( 54) TO H(541) 
CONT C(56) TO N ( 54) TO H(542) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 55) TO H(552) 
CONT N ( 55) TO H(551) 
REST 0.026, 0.002 = H(552,U[ISO]) 
REST 0.026, 0.002 = H(551,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(56) TO N ( 55) TO H(552) 
CONT C(56) TO N ( 55) TO H(551) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 101) TO H(1012) 
CONT O ( 101) TO H(1011) 
REST 0.092, 0.002 = H(1012,U[ISO]) 
REST 0.092, 0.002 = H(1011,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4_pyridine
_database_code_depnum_ccdc_archive 'CCDC 1574951'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
Hydrogen atoms were  visible in the Fourier difference 
map and were initially refined with restraints on bond lengths and angles, 
after which the positions were used as the basis for a riding model. O-H 
hydrogen atoms were visible in the difference map and were refined with 
restraints on bond lengths and distances. 

Restraints were applied to the bond lengths and thermal and vibrational 
ellipsoid parameters of the diethyl ether solvent molecule. Otherwise, it was 
not necessary to use any restraints during the refinement.
;

_cell_length_a                   12.44400(10)
_cell_length_b                   13.02970(10)
_cell_length_c                   23.3004(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.7760(9)
_cell_angle_gamma                90
_cell_volume                     3743.22(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ni -3.0029 0.5091 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C43 H39 N5 Ni0.5 O5'
_chemical_formula_moiety         '0.5(C58 H38 N6 Ni O8), 2(C5 H5 N), C4 H10 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         735.17

_cell_measurement_reflns_used    14873
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      73.7
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.18

_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1543.993
_exptl_absorpt_coefficient_mu    0.925

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction Supernova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            27340
_reflns_number_total             7555
_diffrn_reflns_av_R_equivalents  0.022

_diffrn_reflns_theta_min         3.585
_diffrn_reflns_theta_max         73.869
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        73.869
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -15
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      0.09

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.37

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         7521
_refine_ls_number_restraints     39
_refine_ls_number_parameters     490
_oxford_refine_ls_R_factor_ref   0.0426
_refine_ls_wR_factor_ref         0.1034
_refine_ls_goodness_of_fit_ref   0.9760
_refine_ls_shift/su_max          0.0005635
_refine_ls_shift/su_mean         0.0000517

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7522
_refine_ls_R_factor_all          0.0426
_refine_ls_wR_factor_all         0.1035

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6835
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_gt          0.0982

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.145E+04 0.241E+04 0.145E+04 590. 127. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N111 N 0.62240(11) 1.36082(10) 0.73286(6) 0.0281 1.0000 Uani . . . . . .
C112 C 0.56751(14) 1.44943(13) 0.72993(8) 0.0335 1.0000 Uani . . . . . .
C113 C 0.60075(15) 1.53334(14) 0.76375(9) 0.0384 1.0000 Uani . . . . . .
C114 C 0.69459(17) 1.52543(14) 0.80229(9) 0.0399 1.0000 Uani . . . . . .
C115 C 0.75327(15) 1.43519(14) 0.80487(8) 0.0353 1.0000 Uani . . . . . .
C116 C 0.71464(14) 1.35468(12) 0.76941(7) 0.0288 1.0000 Uani . . . . . .
C121 C -0.0015(3) 0.6168(3) 0.8380(2) 0.1354 1.0000 Uani D U . . . .
C122 C 0.0641(3) 0.5377(2) 0.87083(15) 0.0848 1.0000 Uani D U . . . .
O123 O 0.09643(17) 0.57474(15) 0.92788(11) 0.0906 1.0000 Uani D U . . . .
C124 C 0.1590(3) 0.5046(2) 0.96278(14) 0.0789 1.0000 Uani D U . . . .
C125 C 0.1837(4) 0.5419(4) 1.02345(17) 0.1287 1.0000 Uani D U . . . .
N1 N 0.43846(9) 0.57367(9) 0.56640(5) 0.0182 1.0000 Uani . . . . . .
C2 C 0.37449(11) 0.53153(11) 0.60364(6) 0.0191 1.0000 Uani . . . . . .
C3 C 0.35987(12) 0.60479(11) 0.64880(6) 0.0225 1.0000 Uani . . . . . .
C4 C 0.41487(12) 0.69056(11) 0.63779(6) 0.0232 1.0000 Uani . . . . . .
C5 C 0.46426(11) 0.67075(11) 0.58623(6) 0.0193 1.0000 Uani . . . . . .
C6 C 0.53151(11) 0.74015(11) 0.56170(6) 0.0196 1.0000 Uani . . . . . .
C7 C 0.58615(11) 0.71999(11) 0.51398(6) 0.0193 1.0000 Uani . . . . . .
N8 N 0.41770(9) 0.37003(9) 0.51663(5) 0.0185 1.0000 Uani . . . . . .
C9 C 0.35296(11) 0.35688(11) 0.55901(6) 0.0195 1.0000 Uani . . . . . .
C10 C 0.65667(12) 0.79208(11) 0.49051(6) 0.0233 1.0000 Uani . . . . . .
C11 C 0.30581(12) 0.25527(11) 0.55439(6) 0.0237 1.0000 Uani . . . . . .
C12 C 0.33313(11) 0.43079(11) 0.60044(6) 0.0196 1.0000 Uani . . . . . .
C13 C 0.55323(11) 0.84191(11) 0.59099(6) 0.0198 1.0000 Uani . . . . . .
C14 C 0.63362(15) 0.84862(12) 0.63815(8) 0.0350 1.0000 Uani . . . . . .
C15 C 0.65724(15) 0.94163(13) 0.66588(8) 0.0359 1.0000 Uani . . . . . .
C16 C 0.60106(12) 1.02921(11) 0.64737(6) 0.0220 1.0000 Uani . . . . . .
C17 C 0.52075(15) 1.02344(13) 0.60007(8) 0.0346 1.0000 Uani . . . . . .
C18 C 0.49769(15) 0.93022(13) 0.57218(8) 0.0350 1.0000 Uani . . . . . .
C19 C 0.62943(13) 1.12641(11) 0.68018(6) 0.0243 1.0000 Uani . . . . . .
O20 O 0.71010(10) 1.13318(9) 0.71564(5) 0.0347 1.0000 Uani . . . . . .
O21 O 0.55940(9) 1.20144(8) 0.66761(5) 0.0310 1.0000 Uani D . . . . .
C22 C 0.26524(11) 0.39761(11) 0.64542(6) 0.0206 1.0000 Uani . . . . . .
C23 C 0.29741(12) 0.31491(12) 0.68170(6) 0.0233 1.0000 Uani . . . . . .
C24 C 0.23437(12) 0.28306(12) 0.72328(6) 0.0251 1.0000 Uani . . . . . .
C25 C 0.13791(12) 0.33343(12) 0.72931(6) 0.0237 1.0000 Uani . . . . . .
C26 C 0.10529(12) 0.41625(12) 0.69348(7) 0.0257 1.0000 Uani . . . . . .
C27 C 0.16819(12) 0.44760(12) 0.65182(6) 0.0239 1.0000 Uani . . . . . .
C28 C 0.06980(13) 0.30191(14) 0.77452(7) 0.0289 1.0000 Uani . . . . . .
O29 O 0.11764(11) 0.23356(11) 0.81122(5) 0.0399 1.0000 Uani D . . . . .
O30 O -0.01976(10) 0.33677(12) 0.77697(6) 0.0418 1.0000 Uani . . . . . .
N51 N 0.63862(10) 0.44659(10) 0.56238(5) 0.0219 1.0000 Uani . . . . . .
C52 C 0.66907(12) 0.34782(12) 0.56345(7) 0.0255 1.0000 Uani . . . . . .
C53 C 0.75341(13) 0.30916(13) 0.60253(7) 0.0299 1.0000 Uani . . . . . .
C54 C 0.80885(13) 0.37497(14) 0.64269(7) 0.0320 1.0000 Uani . . . . . .
C55 C 0.77875(13) 0.47731(15) 0.64189(7) 0.0328 1.0000 Uani . . . . . .
C56 C 0.69333(13) 0.50947(13) 0.60122(7) 0.0278 1.0000 Uani . . . . . .
N101 N 0.01936(13) 0.19747(13) 0.90186(6) 0.0363 1.0000 Uani . . . . . .
C102 C -0.08626(15) 0.20431(14) 0.90479(8) 0.0363 1.0000 Uani . . . . . .
C103 C -0.13122(16) 0.17841(17) 0.95335(9) 0.0434 1.0000 Uani . . . . . .
C104 C -0.06347(19) 0.1446(2) 1.00127(9) 0.0579 1.0000 Uani . . . . . .
C105 C 0.04622(19) 0.1398(2) 0.99903(9) 0.0621 1.0000 Uani . . . . . .
C106 C 0.08445(16) 0.1662(2) 0.94858(8) 0.0479 1.0000 Uani . . . . . .
Ni1 Ni 0.5000 0.5000 0.5000 0.0171 1.0000 Uani S . . . . .
H1121 H 0.5004 1.4545 0.7015 0.0425 1.0000 Uiso R . . . . .
H1131 H 0.5590 1.5934 0.7581 0.0478 1.0000 Uiso R . . . . .
H1141 H 0.7192 1.5827 0.8267 0.0495 1.0000 Uiso R . . . . .
H1151 H 0.8162 1.4263 0.8294 0.0461 1.0000 Uiso R . . . . .
H1161 H 0.7528 1.2910 0.7709 0.0363 1.0000 Uiso R . . . . .
H31 H 0.3179 0.5925 0.6799 0.0290 1.0000 Uiso R . . . . .
H41 H 0.4201 0.7520 0.6587 0.0278 1.0000 Uiso R . . . . .
H101 H 0.6727 0.8586 0.5047 0.0287 1.0000 Uiso R . . . . .
H111 H 0.2574 0.2292 0.5778 0.0303 1.0000 Uiso R . . . . .
H141 H 0.6758 0.7894 0.6510 0.0445 1.0000 Uiso R . . . . .
H151 H 0.7141 0.9477 0.6999 0.0450 1.0000 Uiso R . . . . .
H171 H 0.4832 1.0846 0.5856 0.0442 1.0000 Uiso R . . . . .
H181 H 0.4421 0.9279 0.5386 0.0433 1.0000 Uiso R . . . . .
H231 H 0.3643 0.2801 0.6790 0.0287 1.0000 Uiso R . . . . .
H241 H 0.2579 0.2288 0.7483 0.0312 1.0000 Uiso R . . . . .
H261 H 0.0416 0.4530 0.6973 0.0309 1.0000 Uiso R . . . . .
H271 H 0.1466 0.5047 0.6263 0.0310 1.0000 Uiso R . . . . .
H521 H 0.6275 0.3043 0.5349 0.0323 1.0000 Uiso R . . . . .
H531 H 0.7705 0.2385 0.6004 0.0379 1.0000 Uiso R . . . . .
H541 H 0.8693 0.3484 0.6710 0.0410 1.0000 Uiso R . . . . .
H551 H 0.8139 0.5225 0.6697 0.0410 1.0000 Uiso R . . . . .
H561 H 0.6696 0.5796 0.5979 0.0333 1.0000 Uiso R . . . . .
H1021 H -0.1303 0.2284 0.8707 0.0471 1.0000 Uiso R . . . . .
H1031 H -0.2066 0.1827 0.9521 0.0547 1.0000 Uiso R . . . . .
H1041 H -0.0912 0.1256 1.0356 0.0715 1.0000 Uiso R . . . . .
H1051 H 0.0965 0.1156 1.0330 0.0779 1.0000 Uiso R . . . . .
H1061 H 0.1650 0.1636 0.9466 0.0598 1.0000 Uiso R . . . . .
H291 H 0.0797(17) 0.2267(19) 0.8376(8) 0.0500 1.0000 Uiso D . . . . .
H211 H 0.5795(19) 1.2539(14) 0.6876(9) 0.0500 1.0000 Uiso D . . . . .
H1211 H -0.0245 0.5946 0.7995 0.1552 1.0000 Uiso R . . . . .
H1212 H 0.0401 0.6778 0.8373 0.1552 1.0000 Uiso R . . . . .
H1213 H -0.0632 0.6300 0.8568 0.1552 1.0000 Uiso R . . . . .
H1221 H 0.1264 0.5242 0.8525 0.1033 1.0000 Uiso R . . . . .
H1222 H 0.0230 0.4765 0.8721 0.1033 1.0000 Uiso R . . . . .
H1241 H 0.2253 0.4939 0.9477 0.0967 1.0000 Uiso R . . . . .
H1242 H 0.1207 0.4415 0.9626 0.0967 1.0000 Uiso R . . . . .
H1251 H 0.2265 0.4927 1.0464 0.1497 1.0000 Uiso R . . . . .
H1252 H 0.2223 0.6049 1.0239 0.1497 1.0000 Uiso R . . . . .
H1253 H 0.1177 0.5525 1.0388 0.1497 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.19(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N111 . C112 . 1.339(2) yes
N111 . C116 . 1.336(2) yes
C112 . C113 . 1.378(2) yes
C112 . H1121 . 0.996 no
C113 . C114 . 1.377(3) yes
C113 . H1131 . 0.939 no
C114 . C115 . 1.381(3) yes
C114 . H1141 . 0.963 no
C115 . C116 . 1.381(2) yes
C115 . H1151 . 0.913 no
C116 . H1161 . 0.955 no
C121 . C122 . 1.465(4) yes
C121 . H1211 . 0.950 no
C121 . H1212 . 0.950 no
C121 . H1213 . 0.950 no
C122 . O123 . 1.420(4) yes
C122 . H1221 . 0.950 no
C122 . H1222 . 0.950 no
O123 . C124 . 1.390(3) yes
C124 . C125 . 1.487(4) yes
C124 . H1241 . 0.950 no
C124 . H1242 . 0.950 no
C125 . H1251 . 0.950 no
C125 . H1252 . 0.950 no
C125 . H1253 . 0.950 no
N1 . C2 . 1.3692(18) yes
N1 . C5 . 1.3698(18) yes
N1 . Ni1 . 2.0548(11) yes
C2 . C3 . 1.4503(19) yes
C2 . C12 . 1.408(2) yes
C3 . C4 . 1.353(2) yes
C3 . H31 . 0.961 no
C4 . C5 . 1.4449(19) yes
C4 . H41 . 0.936 no
C5 . C6 . 1.405(2) yes
C6 . C7 . 1.4044(19) yes
C6 . C13 . 1.4989(18) yes
C7 . N8 2_666 1.3703(18) yes
C7 . C10 . 1.4427(19) yes
N8 . C9 . 1.3670(18) yes
N8 . Ni1 . 2.0431(11) yes
C9 . C11 . 1.446(2) yes
C9 . C12 . 1.409(2) yes
C10 . C11 2_666 1.351(2) yes
C10 . H101 . 0.939 no
C11 . H111 . 0.930 no
C12 . C22 . 1.4962(19) yes
C13 . C14 . 1.385(2) yes
C13 . C18 . 1.383(2) yes
C14 . C15 . 1.386(2) yes
C14 . H141 . 0.959 no
C15 . C16 . 1.377(2) yes
C15 . H151 . 0.991 no
C16 . C17 . 1.386(2) yes
C16 . C19 . 1.497(2) yes
C17 . C18 . 1.389(2) yes
C17 . H171 . 0.961 no
C18 . H181 . 0.972 no
C19 . O20 . 1.2140(19) yes
C19 . O21 . 1.3160(19) yes
O21 . H211 . 0.845(12) no
C22 . C23 . 1.394(2) yes
C22 . C27 . 1.398(2) yes
C23 . C24 . 1.390(2) yes
C23 . H231 . 0.958 no
C24 . C25 . 1.392(2) yes
C24 . H241 . 0.938 no
C25 . C26 . 1.391(2) yes
C25 . C28 . 1.496(2) yes
C26 . C27 . 1.388(2) yes
C26 . H261 . 0.940 no
C27 . H271 . 0.967 no
C28 . O29 . 1.319(2) yes
C28 . O30 . 1.212(2) yes
O29 . H291 . 0.828(12) no
N51 . C52 . 1.341(2) yes
N51 . C56 . 1.337(2) yes
N51 . Ni1 . 2.2122(12) yes
C52 . C53 . 1.388(2) yes
C52 . H521 . 0.968 no
C53 . C54 . 1.383(2) yes
C53 . H531 . 0.948 no
C54 . C55 . 1.385(3) yes
C54 . H541 . 0.993 no
C55 . C56 . 1.389(2) yes
C55 . H551 . 0.939 no
C56 . H561 . 0.960 no
N101 . C102 . 1.328(2) yes
N101 . C106 . 1.330(2) yes
C102 . C103 . 1.371(3) yes
C102 . H1021 . 0.956 no
C103 . C104 . 1.377(3) yes
C103 . H1031 . 0.937 no
C104 . C105 . 1.374(3) yes
C104 . H1041 . 0.947 no
C105 . C106 . 1.371(3) yes
C105 . H1051 . 0.992 no
C106 . H1061 . 1.009 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C112 . N111 . C116 . 118.21(14) yes
N111 . C112 . C113 . 122.92(16) yes
N111 . C112 . H1121 . 117.9 no
C113 . C112 . H1121 . 119.2 no
C112 . C113 . C114 . 118.41(17) yes
C112 . C113 . H1131 . 117.6 no
C114 . C113 . H1131 . 123.9 no
C113 . C114 . C115 . 119.26(16) yes
C113 . C114 . H1141 . 120.1 no
C115 . C114 . H1141 . 120.6 no
C114 . C115 . C116 . 118.78(17) yes
C114 . C115 . H1151 . 122.7 no
C116 . C115 . H1151 . 118.6 no
C115 . C116 . N111 . 122.38(15) yes
C115 . C116 . H1161 . 120.4 no
N111 . C116 . H1161 . 117.2 no
C122 . C121 . H1211 . 110.7 no
C122 . C121 . H1212 . 109.3 no
H1211 . C121 . H1212 . 109.5 no
C122 . C121 . H1213 . 108.4 no
H1211 . C121 . H1213 . 109.5 no
H1212 . C121 . H1213 . 109.5 no
C121 . C122 . O123 . 108.5(3) yes
C121 . C122 . H1221 . 109.1 no
O123 . C122 . H1221 . 109.7 no
C121 . C122 . H1222 . 110.0 no
O123 . C122 . H1222 . 110.1 no
H1221 . C122 . H1222 . 109.5 no
C122 . O123 . C124 . 112.9(2) yes
O123 . C124 . C125 . 111.6(3) yes
O123 . C124 . H1241 . 109.0 no
C125 . C124 . H1241 . 108.8 no
O123 . C124 . H1242 . 109.0 no
C125 . C124 . H1242 . 109.0 no
H1241 . C124 . H1242 . 109.5 no
C124 . C125 . H1251 . 110.0 no
C124 . C125 . H1252 . 109.3 no
H1251 . C125 . H1252 . 109.5 no
C124 . C125 . H1253 . 109.1 no
H1251 . C125 . H1253 . 109.5 no
H1252 . C125 . H1253 . 109.5 no
C2 . N1 . C5 . 106.64(11) yes
C2 . N1 . Ni1 . 126.70(9) yes
C5 . N1 . Ni1 . 126.23(9) yes
N1 . C2 . C3 . 109.67(12) yes
N1 . C2 . C12 . 125.44(13) yes
C3 . C2 . C12 . 124.83(13) yes
C2 . C3 . C4 . 106.85(12) yes
C2 . C3 . H31 . 124.8 no
C4 . C3 . H31 . 128.3 no
C3 . C4 . C5 . 107.03(13) yes
C3 . C4 . H41 . 127.6 no
C5 . C4 . H41 . 125.4 no
C4 . C5 . N1 . 109.80(12) yes
C4 . C5 . C6 . 124.54(13) yes
N1 . C5 . C6 . 125.63(13) yes
C5 . C6 . C7 . 125.49(13) yes
C5 . C6 . C13 . 117.70(12) yes
C7 . C6 . C13 . 116.68(12) yes
C6 . C7 . N8 2_666 125.85(13) yes
C6 . C7 . C10 . 124.26(13) yes
N8 2_666 C7 . C10 . 109.89(12) yes
C7 2_666 N8 . C9 . 106.63(11) yes
C7 2_666 N8 . Ni1 . 126.44(9) yes
C9 . N8 . Ni1 . 126.90(9) yes
N8 . C9 . C11 . 109.50(12) yes
N8 . C9 . C12 . 125.75(13) yes
C11 . C9 . C12 . 124.74(13) yes
C7 . C10 . C11 2_666 106.73(13) yes
C7 . C10 . H101 . 125.4 no
C11 2_666 C10 . H101 . 127.9 no
C9 . C11 . C10 2_666 107.25(13) yes
C9 . C11 . H111 . 125.4 no
C10 2_666 C11 . H111 . 127.4 no
C9 . C12 . C2 . 125.23(13) yes
C9 . C12 . C22 . 116.76(12) yes
C2 . C12 . C22 . 117.99(12) yes
C6 . C13 . C14 . 118.91(13) yes
C6 . C13 . C18 . 122.70(13) yes
C14 . C13 . C18 . 118.38(14) yes
C13 . C14 . C15 . 120.66(15) yes
C13 . C14 . H141 . 120.2 no
C15 . C14 . H141 . 119.1 no
C14 . C15 . C16 . 120.80(15) yes
C14 . C15 . H151 . 121.8 no
C16 . C15 . H151 . 117.4 no
C15 . C16 . C17 . 119.02(14) yes
C15 . C16 . C19 . 117.83(13) yes
C17 . C16 . C19 . 123.15(14) yes
C16 . C17 . C18 . 120.03(15) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 120.1 no
C17 . C18 . C13 . 121.11(15) yes
C17 . C18 . H181 . 118.9 no
C13 . C18 . H181 . 120.0 no
C16 . C19 . O20 . 121.69(14) yes
C16 . C19 . O21 . 114.31(13) yes
O20 . C19 . O21 . 124.00(14) yes
C19 . O21 . H211 . 109.9(16) no
C12 . C22 . C23 . 120.33(13) yes
C12 . C22 . C27 . 121.19(13) yes
C23 . C22 . C27 . 118.47(13) yes
C22 . C23 . C24 . 120.70(14) yes
C22 . C23 . H231 . 120.5 no
C24 . C23 . H231 . 118.8 no
C23 . C24 . C25 . 120.36(14) yes
C23 . C24 . H241 . 120.1 no
C25 . C24 . H241 . 119.5 no
C24 . C25 . C26 . 119.40(13) yes
C24 . C25 . C28 . 121.34(14) yes
C26 . C25 . C28 . 119.24(14) yes
C25 . C26 . C27 . 120.11(14) yes
C25 . C26 . H261 . 121.4 no
C27 . C26 . H261 . 118.5 no
C22 . C27 . C26 . 120.96(14) yes
C22 . C27 . H271 . 117.7 no
C26 . C27 . H271 . 121.4 no
C25 . C28 . O29 . 113.12(14) yes
C25 . C28 . O30 . 122.85(15) yes
O29 . C28 . O30 . 124.03(15) yes
C28 . O29 . H291 . 107.5(17) no
C52 . N51 . C56 . 117.31(13) yes
C52 . N51 . Ni1 . 120.50(10) yes
C56 . N51 . Ni1 . 122.17(10) yes
N51 . C52 . C53 . 123.19(15) yes
N51 . C52 . H521 . 115.2 no
C53 . C52 . H521 . 121.6 no
C52 . C53 . C54 . 118.86(16) yes
C52 . C53 . H531 . 118.2 no
C54 . C53 . H531 . 122.9 no
C53 . C54 . C55 . 118.61(15) yes
C53 . C54 . H541 . 119.8 no
C55 . C54 . H541 . 121.6 no
C54 . C55 . C56 . 118.70(16) yes
C54 . C55 . H551 . 119.7 no
C56 . C55 . H551 . 121.6 no
C55 . C56 . N51 . 123.32(15) yes
C55 . C56 . H561 . 122.7 no
N51 . C56 . H561 . 113.9 no
C102 . N101 . C106 . 118.41(15) yes
N101 . C102 . C103 . 122.90(17) yes
N101 . C102 . H1021 . 116.1 no
C103 . C102 . H1021 . 121.0 no
C102 . C103 . C104 . 118.34(18) yes
C102 . C103 . H1031 . 118.7 no
C104 . C103 . H1031 . 123.0 no
C103 . C104 . C105 . 119.06(19) yes
C103 . C104 . H1041 . 121.0 no
C105 . C104 . H1041 . 119.9 no
C104 . C105 . C106 . 118.9(2) yes
C104 . C105 . H1051 . 120.4 no
C106 . C105 . H1051 . 120.7 no
C105 . C106 . N101 . 122.38(19) yes
C105 . C106 . H1061 . 119.5 no
N101 . C106 . H1061 . 118.1 no
N51 . Ni1 . N51 2_666 179.995 yes
N51 . Ni1 . N1 . 89.38(4) yes
N51 2_666 Ni1 . N1 . 90.62(4) yes
N51 . Ni1 . N1 2_666 90.62(4) yes
N51 2_666 Ni1 . N1 2_666 89.38(4) yes
N1 . Ni1 . N1 2_666 179.994 yes
N51 . Ni1 . N8 2_666 91.09(5) yes
N51 2_666 Ni1 . N8 2_666 88.91(5) yes
N1 . Ni1 . N8 2_666 90.18(5) yes
N1 2_666 Ni1 . N8 2_666 89.82(5) yes
N51 . Ni1 . N8 . 88.91(5) yes
N51 2_666 Ni1 . N8 . 91.09(5) yes
N1 . Ni1 . N8 . 89.82(5) yes
N1 2_666 Ni1 . N8 . 90.18(5) yes
N8 2_666 Ni1 . N8 . 179.994 yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C116 . H1161 . O20 . 129.74(5) 0.955 2.447 3.144(3) yes
C3 . H31 . O20 4_646 147.04(4) 0.961 2.562 3.408(3) yes
O29 . H291 . N101 . 169(2) 0.828 1.805 2.622(3) yes
O21 . H211 . N111 . 177(2) 0.845 1.785 2.630(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 08/12/16 at 18: 3:55
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (  111 ,X'S,U'S)  UNTIL NI   (    1 ) 
CONT H    (  291 ,X'S)  UNTIL H    (  211 ) 
RIDE C   ( 112,X'S) H   (1121,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) 
RIDE C   ( 115,X'S) H   (1151,X'S) 
RIDE C   ( 116,X'S) H   (1161,X'S) 
RIDE C   ( 121,X'S) H   (1211,X'S) H   (1212,X'S) H   (1213,X'S) 
RIDE C   ( 122,X'S) H   (1221,X'S) H   (1222,X'S) 
RIDE C   ( 124,X'S) H   (1241,X'S) H   (1242,X'S) 
RIDE C   ( 125,X'S) H   (1251,X'S) H   (1252,X'S) H   (1253,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   ( 102,X'S) H   (1021,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) 
RIDE C   ( 105,X'S) H   (1051,X'S) 
RIDE C   ( 106,X'S) H   (1061,X'S) 
END         
;

_iucr_refine_instructions_details_restraints 
;                                                                    
#
# Punched on 08/12/16 at 18: 3:55
#
#LIST     16                                                                    
DIST 1.50, 0.01 = C(121) TO C(122), C(124) TO C(125) 
DIST 1.43, 0.01 = C(122) TO O(123), O(123) TO C(124) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00100 = C(121) TO C(122) 
VIBR .0, 0.00100 = C(122) TO O(123) 
VIBR .0, 0.00200 = O(123) TO C(121) 
VIBR .0, 0.00100 = O(123) TO C(124) 
VIBR .0, 0.00200 = C(124) TO C(122) 
VIBR .0, 0.00100 = C(124) TO C(125) 
VIBR .0, 0.00200 = C(125) TO O(123) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.02000 = C(121) TO C(122) 
U(IJ) .0, 0.01000 = C(122) TO O(123) 
U(IJ) .0, 0.01000 = O(123) TO C(124) 
U(IJ) .0, 0.02000 = C(124) TO C(125) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 21) TO H(211) 
REST 0.047, 0.002 = H(211,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 29) TO H(291) 
REST 0.060, 0.002 = H(291,U[ISO]) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 21) TO H(211) 
REST 0.047, 0.002 = H(211,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 29) TO H(291) 
REST 0.060, 0.002 = H(291,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3_5
_database_code_depnum_ccdc_archive 'CCDC 1589159'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;
#==============================================================================
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.014 0.000 0.000 329 71 ' '
_platon_squeeze_details          
;
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
;An area of diffuse electron density was present, which appeared to be due to 
disordered solvent molecules was present. This could not be sensibly 
refined, and so PLATON-SQUEEZE was used to include this electron density 
in the refinement.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H and O-H hydrogen 
atoms were visible in the Fourier differnence map and were refined with 
restraints on bond lengths and angles. 

Otherwise, it was not necessary to apply any crystallographic restraints.,SQUEEZE
;

_cell_length_a                   10.0854(2)
_cell_length_b                   20.0861(5)
_cell_length_c                   20.4927(5)
_cell_angle_alpha                109.178(2)
_cell_angle_beta                 103.485(2)
_cell_angle_gamma                103.585(2)
_cell_volume                     3586.88(9)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C79 H67 N15 O9'
_chemical_formula_moiety         'C48 H26 N4 O8, 2(C8 H12 N4), 3(C5 H5 N), H2 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         1370.50

_cell_measurement_reflns_used    15751
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      73.7
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.41

_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1436
_exptl_absorpt_coefficient_mu    0.696

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            118047
_reflns_number_total             13058
_diffrn_reflns_av_R_equivalents  0.029

_diffrn_reflns_theta_min         2.476
_diffrn_reflns_theta_max         68.240
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -12
_reflns_limit_h_max              11
_reflns_limit_k_min              -24
_reflns_limit_k_max              22
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.09
_oxford_diffrn_Wilson_scale      0.11

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.52
_refine_diff_density_max         0.81

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         13004
_refine_ls_number_restraints     40
_refine_ls_number_parameters     988
_oxford_refine_ls_R_factor_ref   0.0651
_refine_ls_wR_factor_ref         0.1202
_refine_ls_goodness_of_fit_ref   0.9755
_refine_ls_shift/su_max          0.0003970
_refine_ls_shift/su_mean         0.0000260

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        13007
_refine_ls_R_factor_all          0.0652
_refine_ls_wR_factor_all         0.1204

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                10787
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_gt          0.1124

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 961. 0.152E+04 880. 328. 60.4 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N101 N 0.2720(2) 0.19170(12) 0.22175(11) 0.0313 1.0000 Uani D . . . . .
N102 N 0.3437(2) 0.23486(12) 0.34710(11) 0.0295 1.0000 Uani D . . . . .
C103 C 0.3688(2) 0.23399(13) 0.28641(12) 0.0245 1.0000 Uani D . . . . .
N104 N 0.7591(2) 0.46670(11) 0.49117(11) 0.0253 1.0000 Uani D . . . . .
N105 N 0.8965(2) 0.52030(11) 0.43638(11) 0.0274 1.0000 Uani D . . . . .
C106 C 0.7928(2) 0.46393(12) 0.43230(12) 0.0226 1.0000 Uani D . . . . .
C107 C 0.5107(2) 0.28248(13) 0.29258(12) 0.0241 1.0000 Uani . . . . . .
C108 C 0.5818(2) 0.34960(12) 0.35395(12) 0.0226 1.0000 Uani . . . . . .
C109 C 0.7160(2) 0.39640(12) 0.36287(12) 0.0230 1.0000 Uani . . . . . .
C110 C 0.7779(3) 0.37739(14) 0.30813(13) 0.0279 1.0000 Uani . . . . . .
C111 C 0.7050(3) 0.31072(15) 0.24592(13) 0.0321 1.0000 Uani . . . . . .
C112 C 0.5729(3) 0.26300(14) 0.23834(13) 0.0288 1.0000 Uani . . . . . .
N211 N 0.9935(3) 0.44326(15) 0.67104(14) 0.0452 1.0000 Uani . . . . . .
C212 C 0.8586(3) 0.39645(15) 0.64353(15) 0.0375 1.0000 Uani . . . . . .
C213 C 0.8011(3) 0.35171(16) 0.67553(17) 0.0444 1.0000 Uani . . . . . .
C214 C 0.8886(4) 0.3531(2) 0.7376(2) 0.0642 1.0000 Uani . . . . . .
C215 C 1.0293(5) 0.3994(3) 0.7663(2) 0.0796 1.0000 Uani . . . . . .
C216 C 1.0768(4) 0.4435(2) 0.7316(2) 0.0706 1.0000 Uani . . . . . .
O31 O 1.53553(17) 0.35378(9) 0.49928(9) 0.0285 1.0000 Uani . . . . . .
O32 O 1.42102(18) 0.43321(9) 0.53756(9) 0.0298 1.0000 Uani . . . . . .
C33 C 1.4368(2) 0.37058(12) 0.52197(11) 0.0218 1.0000 Uani . . . . . .
C34 C 1.3305(2) 0.31009(12) 0.53124(11) 0.0197 1.0000 Uani . . . . . .
C35 C 1.3405(2) 0.23891(12) 0.51469(12) 0.0210 1.0000 Uani . . . . . .
C36 C 1.2402(2) 0.18340(12) 0.52173(12) 0.0212 1.0000 Uani . . . . . .
C37 C 1.1280(2) 0.19787(12) 0.54610(11) 0.0192 1.0000 Uani . . . . . .
C38 C 1.1192(2) 0.26970(12) 0.56359(12) 0.0222 1.0000 Uani . . . . . .
C39 C 1.2194(2) 0.32492(12) 0.55634(12) 0.0220 1.0000 Uani . . . . . .
O41 O 0.4203(2) -0.25737(10) 0.02664(9) 0.0346 1.0000 Uani . . . . . .
O42 O 0.4372(2) -0.35126(9) 0.05962(9) 0.0346 1.0000 Uani . . . . . .
C43 C 0.4431(3) -0.28441(14) 0.07412(13) 0.0277 1.0000 Uani . . . . . .
C44 C 0.4804(2) -0.23332(13) 0.15390(12) 0.0232 1.0000 Uani . . . . . .
C45 C 0.4979(3) -0.26149(13) 0.20761(13) 0.0280 1.0000 Uani . . . . . .
C46 C 0.5374(3) -0.21451(13) 0.28115(12) 0.0254 1.0000 Uani . . . . . .
C47 C 0.5610(2) -0.13772(12) 0.30277(12) 0.0207 1.0000 Uani . . . . . .
C48 C 0.5397(2) -0.11034(12) 0.24829(12) 0.0229 1.0000 Uani . . . . . .
C49 C 0.5003(2) -0.15741(13) 0.17505(12) 0.0241 1.0000 Uani . . . . . .
O51 O -0.05718(18) -0.38041(9) 0.57772(9) 0.0292 1.0000 Uani . . . . . .
O52 O -0.09099(19) -0.28088(10) 0.65085(10) 0.0355 1.0000 Uani . . . . . .
C53 C -0.0261(2) -0.31062(13) 0.61084(12) 0.0238 1.0000 Uani . . . . . .
C54 C 0.0989(2) -0.25902(12) 0.60270(12) 0.0211 1.0000 Uani . . . . . .
C55 C 0.1412(2) -0.18193(13) 0.64138(12) 0.0246 1.0000 Uani . . . . . .
C56 C 0.2570(2) -0.13385(12) 0.63586(13) 0.0251 1.0000 Uani . . . . . .
C57 C 0.3322(2) -0.16065(12) 0.59011(12) 0.0201 1.0000 Uani . . . . . .
C58 C 0.2884(2) -0.23832(12) 0.55065(12) 0.0210 1.0000 Uani . . . . . .
C59 C 0.1743(2) -0.28608(12) 0.55744(12) 0.0214 1.0000 Uani . . . . . .
O61 O 1.27445(18) 0.23101(10) 1.10270(9) 0.0307 1.0000 Uani . . . . . .
O62 O 1.0823(2) 0.26465(11) 1.11316(9) 0.0410 1.0000 Uani . . . . . .
C63 C 1.1515(3) 0.23513(14) 1.07585(13) 0.0292 1.0000 Uani . . . . . .
C64 C 1.0853(3) 0.20235(14) 0.99327(12) 0.0282 1.0000 Uani . . . . . .
C65 C 1.1688(3) 0.18558(14) 0.94932(13) 0.0298 1.0000 Uani . . . . . .
C66 C 1.1077(3) 0.15467(14) 0.87340(13) 0.0289 1.0000 Uani . . . . . .
C67 C 0.9608(2) 0.13932(13) 0.83933(12) 0.0246 1.0000 Uani . . . . . .
C68 C 0.8782(3) 0.15765(15) 0.88391(13) 0.0327 1.0000 Uani . . . . . .
C69 C 0.9398(3) 0.18828(16) 0.95957(13) 0.0356 1.0000 Uani . . . . . .
N121 N 0.5942(2) 0.44683(12) 0.08142(11) 0.0308 1.0000 Uani D . . . . .
N122 N 0.4950(2) 0.33759(11) 0.08925(11) 0.0284 1.0000 Uani D . . . . .
C123 C 0.5270(2) 0.41022(13) 0.11374(12) 0.0242 1.0000 Uani D . . . . .
N124 N 0.1946(2) 0.34704(12) 0.26572(11) 0.0306 1.0000 Uani D . . . . .
N125 N 0.3357(2) 0.44025(11) 0.37823(10) 0.0263 1.0000 Uani D . . . . .
C126 C 0.2988(2) 0.41106(13) 0.30598(12) 0.0239 1.0000 Uani D . . . . .
C127 C 0.4892(2) 0.45159(13) 0.17777(12) 0.0242 1.0000 Uani . . . . . .
C128 C 0.4136(2) 0.41324(13) 0.21066(12) 0.0231 1.0000 Uani . . . . . .
C129 C 0.3787(2) 0.45229(13) 0.27064(12) 0.0230 1.0000 Uani . . . . . .
C130 C 0.4193(3) 0.52992(13) 0.29768(13) 0.0286 1.0000 Uani . . . . . .
C131 C 0.4951(3) 0.56808(14) 0.26533(14) 0.0364 1.0000 Uani . . . . . .
C132 C 0.5305(3) 0.52984(14) 0.20604(13) 0.0333 1.0000 Uani . . . . . .
N201 N 0.9876(3) 0.10528(14) 0.19872(14) 0.0489 1.0000 Uani . . . . . .
C202 C 0.8962(4) 0.13991(19) 0.17651(18) 0.0549 1.0000 Uani . . . . . .
C203 C 0.7513(4) 0.1125(2) 0.1621(2) 0.0656 1.0000 Uani . . . . . .
C204 C 0.6931(4) 0.0466(2) 0.1710(2) 0.0635 1.0000 Uani . . . . . .
C205 C 0.7839(4) 0.01287(18) 0.1926(2) 0.0558 1.0000 Uani . . . . . .
C206 C 0.9298(4) 0.04330(17) 0.20625(19) 0.0527 1.0000 Uani . . . . . .
N221 N 0.1732(4) 0.4195(2) -0.0111(2) 0.0819 1.0000 Uani . . . . . .
C222 C 0.2128(5) 0.4791(3) 0.0478(3) 0.0922 1.0000 Uani . . . . . .
C223 C 0.1340(7) 0.4922(4) 0.0935(3) 0.1278 1.0000 Uani . . . . . .
C224 C 0.0040(8) 0.4404(4) 0.0753(4) 0.1250 1.0000 Uani . . . . . .
C225 C -0.0486(6) 0.3779(3) 0.0076(4) 0.1136 1.0000 Uani . . . . . .
C226 C 0.0438(5) 0.3724(3) -0.0304(3) 0.0894 1.0000 Uani . . . . . .
O231 O 0.6660(2) 0.60147(11) 0.10507(11) 0.0419 1.0000 Uani D . . . . .
N1 N 0.91592(19) 0.10403(10) 0.64099(9) 0.0200 1.0000 Uani . . . . . .
C2 C 0.9538(2) 0.13535(12) 0.71575(12) 0.0215 1.0000 Uani . . . . . .
C3 C 1.0703(3) 0.20718(13) 0.74664(12) 0.0281 1.0000 Uani . . . . . .
C4 C 1.1030(2) 0.21766(13) 0.68993(12) 0.0258 1.0000 Uani . . . . . .
C5 C 1.0075(2) 0.15246(12) 0.62392(12) 0.0205 1.0000 Uani . . . . . .
C6 C 1.0184(2) 0.13876(12) 0.55357(12) 0.0197 1.0000 Uani . . . . . .
N7 N 0.80931(19) 0.02166(10) 0.48297(10) 0.0191 1.0000 Uani D . . . . .
C8 C 0.9339(2) 0.07347(12) 0.49000(12) 0.0195 1.0000 Uani D . . . . .
C9 C 0.9558(2) 0.04903(13) 0.42064(12) 0.0237 1.0000 Uani . . . . . .
C10 C 0.8455(2) -0.01567(13) 0.37425(12) 0.0228 1.0000 Uani . . . . . .
C11 C 0.7480(2) -0.03190(12) 0.41226(11) 0.0189 1.0000 Uani D . . . . .
C12 C 0.6115(2) -0.08793(12) 0.38269(11) 0.0198 1.0000 Uani . . . . . .
N13 N 0.56457(19) -0.07473(10) 0.49808(10) 0.0196 1.0000 Uani . . . . . .
C14 C 0.5217(2) -0.10251(12) 0.42319(12) 0.0195 1.0000 Uani . . . . . .
C15 C 0.3747(2) -0.15440(12) 0.39077(12) 0.0223 1.0000 Uani . . . . . .
C16 C 0.3308(2) -0.15982(12) 0.44662(12) 0.0221 1.0000 Uani . . . . . .
C17 C 0.4515(2) -0.11169(12) 0.51357(12) 0.0197 1.0000 Uani . . . . . .
C18 C 0.4552(2) -0.10799(12) 0.58380(12) 0.0195 1.0000 Uani . . . . . .
N19 N 0.68308(19) -0.00012(10) 0.65688(10) 0.0207 1.0000 Uani D . . . . .
C20 C 0.5691(2) -0.05875(12) 0.64917(12) 0.0210 1.0000 Uani D . . . . .
C21 C 0.5897(3) -0.05984(13) 0.72022(12) 0.0252 1.0000 Uani . . . . . .
C22 C 0.7116(3) -0.00189(13) 0.76833(13) 0.0275 1.0000 Uani . . . . . .
C23 C 0.7705(2) 0.03748(13) 0.72899(12) 0.0227 1.0000 Uani D . . . . .
C24 C 0.8927(2) 0.10266(13) 0.75774(12) 0.0233 1.0000 Uani . . . . . .
H351 H 1.4165 0.2278 0.4986 0.0252 1.0000 Uiso R . . . . .
H361 H 1.2486 0.1362 0.5099 0.0251 1.0000 Uiso R . . . . .
H381 H 1.0444 0.2802 0.5803 0.0260 1.0000 Uiso R . . . . .
H391 H 1.2126 0.3736 0.5685 0.0263 1.0000 Uiso R . . . . .
H451 H 0.4836 -0.3128 0.1939 0.0328 1.0000 Uiso R . . . . .
H461 H 0.5489 -0.2342 0.3163 0.0301 1.0000 Uiso R . . . . .
H481 H 0.5517 -0.0588 0.2615 0.0275 1.0000 Uiso R . . . . .
H491 H 0.4863 -0.1386 0.1385 0.0295 1.0000 Uiso R . . . . .
H551 H 0.0917 -0.1623 0.6711 0.0290 1.0000 Uiso R . . . . .
H561 H 0.2854 -0.0827 0.6636 0.0304 1.0000 Uiso R . . . . .
H581 H 0.3384 -0.2580 0.5205 0.0246 1.0000 Uiso R . . . . .
H591 H 0.1495 -0.3375 0.5315 0.0256 1.0000 Uiso R . . . . .
H651 H 1.2655 0.1938 0.9693 0.0351 1.0000 Uiso R . . . . .
H661 H 1.1664 0.1443 0.8449 0.0344 1.0000 Uiso R . . . . .
H681 H 0.7810 0.1503 0.8625 0.0380 1.0000 Uiso R . . . . .
H691 H 0.8839 0.1999 0.9884 0.0422 1.0000 Uiso R . . . . .
H1081 H 0.5391 0.3631 0.3899 0.0263 1.0000 Uiso R . . . . .
H1101 H 0.8700 0.4095 0.3139 0.0326 1.0000 Uiso R . . . . .
H1111 H 0.7461 0.2979 0.2093 0.0378 1.0000 Uiso R . . . . .
H1121 H 0.5254 0.2178 0.1968 0.0337 1.0000 Uiso R . . . . .
H1281 H 0.3866 0.3611 0.1928 0.0278 1.0000 Uiso R . . . . .
H1301 H 0.3946 0.5564 0.3376 0.0334 1.0000 Uiso R . . . . .
H1311 H 0.5216 0.6204 0.2834 0.0431 1.0000 Uiso R . . . . .
H1321 H 0.5845 0.5569 0.1856 0.0403 1.0000 Uiso R . . . . .
H2021 H 0.9347 0.1851 0.1714 0.0651 1.0000 Uiso R . . . . .
H2031 H 0.6908 0.1377 0.1460 0.0760 1.0000 Uiso R . . . . .
H2041 H 0.5908 0.0266 0.1608 0.0750 1.0000 Uiso R . . . . .
H2051 H 0.7481 -0.0325 0.1983 0.0662 1.0000 Uiso R . . . . .
H2061 H 0.9927 0.0183 0.2214 0.0613 1.0000 Uiso R . . . . .
H2221 H 0.3041 0.5156 0.0590 0.1074 1.0000 Uiso R . . . . .
H2231 H 0.1688 0.5366 0.1359 0.1473 1.0000 Uiso R . . . . .
H2241 H -0.0502 0.4462 0.1073 0.1451 1.0000 Uiso R . . . . .
H2251 H -0.1411 0.3420 -0.0090 0.1332 1.0000 Uiso R . . . . .
H2261 H 0.0150 0.3321 -0.0762 0.1045 1.0000 Uiso R . . . . .
H31 H 1.1127 0.2394 0.7958 0.0332 1.0000 Uiso R . . . . .
H41 H 1.1745 0.2578 0.6919 0.0305 1.0000 Uiso R . . . . .
H91 H 1.0335 0.0738 0.4093 0.0279 1.0000 Uiso R . . . . .
H101 H 0.8355 -0.0447 0.3264 0.0277 1.0000 Uiso R . . . . .
H151 H 0.3222 -0.1792 0.3408 0.0255 1.0000 Uiso R . . . . .
H161 H 0.2395 -0.1878 0.4436 0.0257 1.0000 Uiso R . . . . .
H211 H 0.5285 -0.0931 0.7322 0.0299 1.0000 Uiso R . . . . .
H221 H 0.7495 0.0097 0.8180 0.0333 1.0000 Uiso R . . . . .
H1221 H 0.437(3) 0.3116(11) 0.1037(14) 0.0342 1.0000 Uiso D . . . . .
H1222 H 0.521(3) 0.3147(11) 0.0539(12) 0.0343 1.0000 Uiso D . . . . .
H1212 H 0.602(3) 0.4214(11) 0.0399(11) 0.0360 1.0000 Uiso D . . . . .
H1011 H 0.289(2) 0.1975(14) 0.1841(10) 0.0372 1.0000 Uiso D . . . . .
H1252 H 0.412(2) 0.4796(12) 0.4044(11) 0.0310 1.0000 Uiso D . . . . .
H1012 H 0.186(2) 0.1630(14) 0.2178(11) 0.0371 1.0000 Uiso D . . . . .
H1211 H 0.609(3) 0.4939(10) 0.0938(14) 0.0362 1.0000 Uiso D . . . . .
H1052 H 0.938(3) 0.5589(11) 0.4783(10) 0.0326 1.0000 Uiso D . . . . .
H1242 H 0.156(3) 0.3218(12) 0.2876(11) 0.0360 1.0000 Uiso D . . . . .
H1042 H 0.799(3) 0.5087(10) 0.5302(10) 0.0301 1.0000 Uiso D . . . . .
H1251 H 0.290(2) 0.4162(12) 0.3985(11) 0.0311 1.0000 Uiso D . . . . .
H1241 H 0.171(3) 0.3287(12) 0.2190(9) 0.0366 1.0000 Uiso D . . . . .
H1021 H 0.412(2) 0.2625(14) 0.3886(10) 0.0350 1.0000 Uiso D . . . . .
H1022 H 0.2538(19) 0.2201(15) 0.3455(12) 0.0351 1.0000 Uiso D . . . . .
H1051 H 0.920(3) 0.5192(12) 0.3983(10) 0.0323 1.0000 Uiso D . . . . .
H2121 H 0.8000 0.3936 0.5990 0.0442 1.0000 Uiso R . . . . .
H2131 H 0.7028 0.3210 0.6544 0.0526 1.0000 Uiso R . . . . .
H2141 H 0.8526 0.3224 0.7598 0.0766 1.0000 Uiso R . . . . .
H2151 H 1.0944 0.4014 0.8080 0.0936 1.0000 Uiso R . . . . .
H2161 H 1.1748 0.4767 0.7518 0.0818 1.0000 Uiso R . . . . .
H2311 H 0.601(3) 0.619(2) 0.095(2) 0.0618 1.0000 Uiso D . . . . .
H2312 H 0.713(4) 0.598(2) 0.0773(17) 0.0621 1.0000 Uiso D . . . . .
H71 H 0.772(2) 0.0243(11) 0.5163(9) 0.0247 1.0000 Uiso D . . . . .
H191 H 0.698(2) 0.0106(11) 0.6219(9) 0.0261 1.0000 Uiso D . . . . .
H1041 H 0.687(2) 0.4315(11) 0.4893(11) 0.0279 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.846(15)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N101 . C103 . 1.303(3) yes
N101 . H1011 . 0.864(17) no
N101 . H1012 . 0.887(17) no
N102 . C103 . 1.322(3) yes
N102 . H1021 . 0.863(17) no
N102 . H1022 . 0.874(17) no
C103 . C107 . 1.480(3) yes
N104 . C106 . 1.315(3) yes
N104 . H1042 . 0.872(16) no
N104 . H1041 . 0.872(16) no
N105 . C106 . 1.313(3) yes
N105 . H1052 . 0.869(16) no
N105 . H1051 . 0.863(16) no
C106 . C109 . 1.479(3) yes
C107 . C108 . 1.387(3) yes
C107 . C112 . 1.392(3) yes
C108 . C109 . 1.387(3) yes
C108 . H1081 . 0.935 no
C109 . C110 . 1.397(3) yes
C110 . C111 . 1.392(3) yes
C110 . H1101 . 0.954 no
C111 . C112 . 1.387(3) yes
C111 . H1111 . 0.932 no
C112 . H1121 . 0.936 no
N211 . C212 . 1.321(4) yes
N211 . C216 . 1.324(4) yes
C212 . C213 . 1.376(4) yes
C212 . H2121 . 0.940 no
C213 . C214 . 1.356(5) yes
C213 . H2131 . 0.942 no
C214 . C215 . 1.363(5) yes
C214 . H2141 . 0.933 no
C215 . C216 . 1.376(5) yes
C215 . H2151 . 0.932 no
C216 . H2161 . 0.954 no
O31 . C33 . 1.262(3) yes
O32 . C33 . 1.250(3) yes
C33 . C34 . 1.515(3) yes
C34 . C35 . 1.391(3) yes
C34 . C39 . 1.390(3) yes
C35 . C36 . 1.389(3) yes
C35 . H351 . 0.947 no
C36 . C37 . 1.392(3) yes
C36 . H361 . 0.928 no
C37 . C38 . 1.398(3) yes
C37 . C6 . 1.496(3) yes
C38 . C39 . 1.388(3) yes
C38 . H381 . 0.937 no
C39 . H391 . 0.951 no
O41 . C43 . 1.263(3) yes
O42 . C43 . 1.260(3) yes
C43 . C44 . 1.516(3) yes
C44 . C45 . 1.389(3) yes
C44 . C49 . 1.391(3) yes
C45 . C46 . 1.389(3) yes
C45 . H451 . 0.939 no
C46 . C47 . 1.400(3) yes
C46 . H461 . 0.926 no
C47 . C48 . 1.394(3) yes
C47 . C12 . 1.496(3) yes
C48 . C49 . 1.385(3) yes
C48 . H481 . 0.950 no
C49 . H491 . 0.940 no
O51 . C53 . 1.262(3) yes
O52 . C53 . 1.253(3) yes
C53 . C54 . 1.513(3) yes
C54 . C55 . 1.390(3) yes
C54 . C59 . 1.388(3) yes
C55 . C56 . 1.383(3) yes
C55 . H551 . 0.923 no
C56 . C57 . 1.391(3) yes
C56 . H561 . 0.930 no
C57 . C58 . 1.401(3) yes
C57 . C18 . 1.491(3) yes
C58 . C59 . 1.381(3) yes
C58 . H581 . 0.932 no
C59 . H591 . 0.931 no
O61 . C63 . 1.268(3) yes
O62 . C63 . 1.252(3) yes
C63 . C64 . 1.509(3) yes
C64 . C65 . 1.386(3) yes
C64 . C69 . 1.383(3) yes
C65 . C66 . 1.387(3) yes
C65 . H651 . 0.917 no
C66 . C67 . 1.392(3) yes
C66 . H661 . 0.935 no
C67 . C68 . 1.394(3) yes
C67 . C24 . 1.492(3) yes
C68 . C69 . 1.383(3) yes
C68 . H681 . 0.930 no
C69 . H691 . 0.922 no
N121 . C123 . 1.317(3) yes
N121 . H1212 . 0.868(17) no
N121 . H1211 . 0.860(17) no
N122 . C123 . 1.306(3) yes
N122 . H1221 . 0.863(17) no
N122 . H1222 . 0.853(17) no
C123 . C127 . 1.491(3) yes
N124 . C126 . 1.305(3) yes
N124 . H1242 . 0.868(17) no
N124 . H1241 . 0.854(17) no
N125 . C126 . 1.321(3) yes
N125 . H1252 . 0.865(16) no
N125 . H1251 . 0.857(16) no
C126 . C129 . 1.488(3) yes
C127 . C128 . 1.391(3) yes
C127 . C132 . 1.400(3) yes
C128 . C129 . 1.396(3) yes
C128 . H1281 . 0.934 no
C129 . C130 . 1.390(3) yes
C130 . C131 . 1.380(3) yes
C130 . H1301 . 0.941 no
C131 . C132 . 1.383(3) yes
C131 . H1311 . 0.938 no
C132 . H1321 . 0.939 no
N201 . C202 . 1.361(4) yes
N201 . C206 . 1.319(4) yes
C202 . C203 . 1.357(5) yes
C202 . H2021 . 0.949 no
C203 . C204 . 1.407(5) yes
C203 . H2031 . 0.947 no
C204 . C205 . 1.339(5) yes
C204 . H2041 . 0.958 no
C205 . C206 . 1.374(5) yes
C205 . H2051 . 0.952 no
C206 . H2061 . 0.955 no
N221 . C222 . 1.285(6) yes
N221 . C226 . 1.299(6) yes
C222 . C223 . 1.364(7) yes
C222 . H2221 . 0.955 no
C223 . C224 . 1.348(8) yes
C223 . H2231 . 0.936 no
C224 . C225 . 1.407(8) yes
C224 . H2241 . 0.943 no
C225 . C226 . 1.348(7) yes
C225 . H2251 . 0.939 no
C226 . H2261 . 0.940 no
O231 . H2311 . 0.833(18) no
O231 . H2312 . 0.816(18) no
N1 . C2 . 1.367(3) yes
N1 . C5 . 1.369(3) yes
C2 . C3 . 1.456(3) yes
C2 . C24 . 1.407(3) yes
C3 . C4 . 1.346(3) yes
C3 . H31 . 0.927 no
C4 . C5 . 1.452(3) yes
C4 . H41 . 0.929 no
C5 . C6 . 1.412(3) yes
C6 . C8 . 1.406(3) yes
N7 . C8 . 1.373(3) yes
N7 . C11 . 1.373(3) yes
N7 . H71 . 0.847(16) no
C8 . C9 . 1.432(3) yes
C9 . C10 . 1.359(3) yes
C9 . H91 . 0.945 no
C10 . C11 . 1.434(3) yes
C10 . H101 . 0.930 no
C11 . C12 . 1.401(3) yes
C12 . C14 . 1.407(3) yes
N13 . C14 . 1.367(3) yes
N13 . C17 . 1.371(3) yes
C14 . C15 . 1.444(3) yes
C15 . C16 . 1.347(3) yes
C15 . H151 . 0.930 no
C16 . C17 . 1.448(3) yes
C16 . H161 . 0.934 no
C17 . C18 . 1.408(3) yes
C18 . C20 . 1.404(3) yes
N19 . C20 . 1.375(3) yes
N19 . C23 . 1.370(3) yes
N19 . H191 . 0.848(16) no
C20 . C21 . 1.430(3) yes
C21 . C22 . 1.359(3) yes
C21 . H211 . 0.935 no
C22 . C23 . 1.432(3) yes
C22 . H221 . 0.926 no
C23 . C24 . 1.406(3) yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C103 . N101 . H1011 . 118.2(14) no
C103 . N101 . H1012 . 120.0(14) no
H1011 . N101 . H1012 . 121.2(20) no
C103 . N102 . H1021 . 118.1(14) no
C103 . N102 . H1022 . 118.5(14) no
H1021 . N102 . H1022 . 120(2) no
N102 . C103 . N101 . 121.6(2) yes
N102 . C103 . C107 . 118.8(2) yes
N101 . C103 . C107 . 119.6(2) yes
C106 . N104 . H1042 . 118.0(13) no
C106 . N104 . H1041 . 121.5(13) no
H1042 . N104 . H1041 . 119.5(19) no
C106 . N105 . H1052 . 117.6(14) no
C106 . N105 . H1051 . 120.6(14) no
H1052 . N105 . H1051 . 121.7(19) no
N104 . C106 . N105 . 119.6(2) yes
N104 . C106 . C109 . 119.5(2) yes
N105 . C106 . C109 . 120.9(2) yes
C103 . C107 . C108 . 118.6(2) yes
C103 . C107 . C112 . 121.9(2) yes
C108 . C107 . C112 . 119.6(2) yes
C107 . C108 . C109 . 120.8(2) yes
C107 . C108 . H1081 . 119.5 no
C109 . C108 . H1081 . 119.7 no
C106 . C109 . C108 . 118.5(2) yes
C106 . C109 . C110 . 121.7(2) yes
C108 . C109 . C110 . 119.8(2) yes
C109 . C110 . C111 . 119.3(2) yes
C109 . C110 . H1101 . 120.1 no
C111 . C110 . H1101 . 120.5 no
C110 . C111 . C112 . 120.6(2) yes
C110 . C111 . H1111 . 119.6 no
C112 . C111 . H1111 . 119.8 no
C107 . C112 . C111 . 119.9(2) yes
C107 . C112 . H1121 . 119.9 no
C111 . C112 . H1121 . 120.2 no
C212 . N211 . C216 . 116.2(3) yes
N211 . C212 . C213 . 124.0(3) yes
N211 . C212 . H2121 . 117.0 no
C213 . C212 . H2121 . 119.0 no
C212 . C213 . C214 . 118.6(3) yes
C212 . C213 . H2131 . 120.2 no
C214 . C213 . H2131 . 121.2 no
C213 . C214 . C215 . 118.7(3) yes
C213 . C214 . H2141 . 120.3 no
C215 . C214 . H2141 . 121.1 no
C214 . C215 . C216 . 118.8(3) yes
C214 . C215 . H2151 . 122.0 no
C216 . C215 . H2151 . 119.2 no
C215 . C216 . N211 . 123.6(3) yes
C215 . C216 . H2161 . 119.3 no
N211 . C216 . H2161 . 117.1 no
O31 . C33 . O32 . 124.9(2) yes
O31 . C33 . C34 . 117.11(19) yes
O32 . C33 . C34 . 118.02(19) yes
C33 . C34 . C35 . 121.39(19) yes
C33 . C34 . C39 . 120.10(19) yes
C35 . C34 . C39 . 118.5(2) yes
C34 . C35 . C36 . 120.8(2) yes
C34 . C35 . H351 . 120.1 no
C36 . C35 . H351 . 119.1 no
C35 . C36 . C37 . 120.8(2) yes
C35 . C36 . H361 . 119.2 no
C37 . C36 . H361 . 120.0 no
C36 . C37 . C38 . 118.30(19) yes
C36 . C37 . C6 . 121.63(19) yes
C38 . C37 . C6 . 120.07(19) yes
C37 . C38 . C39 . 120.7(2) yes
C37 . C38 . H381 . 119.1 no
C39 . C38 . H381 . 120.2 no
C34 . C39 . C38 . 120.9(2) yes
C34 . C39 . H391 . 119.1 no
C38 . C39 . H391 . 120.0 no
O41 . C43 . O42 . 124.3(2) yes
O41 . C43 . C44 . 118.1(2) yes
O42 . C43 . C44 . 117.5(2) yes
C43 . C44 . C45 . 120.3(2) yes
C43 . C44 . C49 . 121.0(2) yes
C45 . C44 . C49 . 118.7(2) yes
C44 . C45 . C46 . 120.7(2) yes
C44 . C45 . H451 . 119.4 no
C46 . C45 . H451 . 120.0 no
C45 . C46 . C47 . 120.8(2) yes
C45 . C46 . H461 . 119.6 no
C47 . C46 . H461 . 119.6 no
C46 . C47 . C48 . 118.1(2) yes
C46 . C47 . C12 . 119.45(19) yes
C48 . C47 . C12 . 122.42(19) yes
C47 . C48 . C49 . 120.9(2) yes
C47 . C48 . H481 . 119.6 no
C49 . C48 . H481 . 119.5 no
C44 . C49 . C48 . 120.9(2) yes
C44 . C49 . H491 . 118.6 no
C48 . C49 . H491 . 120.5 no
O51 . C53 . O52 . 124.4(2) yes
O51 . C53 . C54 . 118.2(2) yes
O52 . C53 . C54 . 117.4(2) yes
C53 . C54 . C55 . 119.86(19) yes
C53 . C54 . C59 . 122.0(2) yes
C55 . C54 . C59 . 118.1(2) yes
C54 . C55 . C56 . 120.8(2) yes
C54 . C55 . H551 . 120.0 no
C56 . C55 . H551 . 119.2 no
C55 . C56 . C57 . 121.3(2) yes
C55 . C56 . H561 . 119.2 no
C57 . C56 . H561 . 119.5 no
C56 . C57 . C58 . 117.8(2) yes
C56 . C57 . C18 . 120.67(19) yes
C58 . C57 . C18 . 121.55(19) yes
C57 . C58 . C59 . 120.6(2) yes
C57 . C58 . H581 . 119.7 no
C59 . C58 . H581 . 119.7 no
C54 . C59 . C58 . 121.4(2) yes
C54 . C59 . H591 . 120.0 no
C58 . C59 . H591 . 118.6 no
O61 . C63 . O62 . 124.4(2) yes
O61 . C63 . C64 . 117.3(2) yes
O62 . C63 . C64 . 118.3(2) yes
C63 . C64 . C65 . 120.8(2) yes
C63 . C64 . C69 . 120.8(2) yes
C65 . C64 . C69 . 118.4(2) yes
C64 . C65 . C66 . 120.9(2) yes
C64 . C65 . H651 . 121.3 no
C66 . C65 . H651 . 117.8 no
C65 . C66 . C67 . 120.9(2) yes
C65 . C66 . H661 . 119.3 no
C67 . C66 . H661 . 119.8 no
C66 . C67 . C68 . 117.9(2) yes
C66 . C67 . C24 . 121.3(2) yes
C68 . C67 . C24 . 120.8(2) yes
C67 . C68 . C69 . 120.9(2) yes
C67 . C68 . H681 . 119.5 no
C69 . C68 . H681 . 119.6 no
C64 . C69 . C68 . 121.1(2) yes
C64 . C69 . H691 . 118.9 no
C68 . C69 . H691 . 120.0 no
C123 . N121 . H1212 . 118.7(14) no
C123 . N121 . H1211 . 120.9(14) no
H1212 . N121 . H1211 . 118(2) no
C123 . N122 . H1221 . 120.4(14) no
C123 . N122 . H1222 . 120.0(14) no
H1221 . N122 . H1222 . 118.9(20) no
N121 . C123 . N122 . 119.1(2) yes
N121 . C123 . C127 . 120.1(2) yes
N122 . C123 . C127 . 120.8(2) yes
C126 . N124 . H1242 . 118.4(14) no
C126 . N124 . H1241 . 120.7(14) no
H1242 . N124 . H1241 . 120.7(20) no
C126 . N125 . H1252 . 119.9(14) no
C126 . N125 . H1251 . 118.7(14) no
H1252 . N125 . H1251 . 120.8(19) no
N125 . C126 . N124 . 121.1(2) yes
N125 . C126 . C129 . 118.9(2) yes
N124 . C126 . C129 . 120.0(2) yes
C123 . C127 . C128 . 120.6(2) yes
C123 . C127 . C132 . 120.4(2) yes
C128 . C127 . C132 . 119.0(2) yes
C127 . C128 . C129 . 120.4(2) yes
C127 . C128 . H1281 . 119.9 no
C129 . C128 . H1281 . 119.7 no
C126 . C129 . C128 . 120.1(2) yes
C126 . C129 . C130 . 119.9(2) yes
C128 . C129 . C130 . 120.0(2) yes
C129 . C130 . C131 . 119.7(2) yes
C129 . C130 . H1301 . 120.2 no
C131 . C130 . H1301 . 120.1 no
C130 . C131 . C132 . 120.7(2) yes
C130 . C131 . H1311 . 119.6 no
C132 . C131 . H1311 . 119.7 no
C127 . C132 . C131 . 120.3(2) yes
C127 . C132 . H1321 . 120.3 no
C131 . C132 . H1321 . 119.5 no
C202 . N201 . C206 . 117.3(3) yes
N201 . C202 . C203 . 122.2(3) yes
N201 . C202 . H2021 . 119.3 no
C203 . C202 . H2021 . 118.4 no
C202 . C203 . C204 . 119.1(4) yes
C202 . C203 . H2031 . 120.0 no
C204 . C203 . H2031 . 121.0 no
C203 . C204 . C205 . 118.1(3) yes
C203 . C204 . H2041 . 119.8 no
C205 . C204 . H2041 . 122.1 no
C204 . C205 . C206 . 120.1(3) yes
C204 . C205 . H2051 . 120.4 no
C206 . C205 . H2051 . 119.5 no
C205 . C206 . N201 . 123.2(3) yes
C205 . C206 . H2061 . 118.7 no
N201 . C206 . H2061 . 118.0 no
C222 . N221 . C226 . 116.4(4) yes
N221 . C222 . C223 . 124.4(5) yes
N221 . C222 . H2221 . 115.8 no
C223 . C222 . H2221 . 119.8 no
C222 . C223 . C224 . 118.4(6) yes
C222 . C223 . H2231 . 120.6 no
C224 . C223 . H2231 . 121.0 no
C223 . C224 . C225 . 118.5(5) yes
C223 . C224 . H2241 . 120.5 no
C225 . C224 . H2241 . 121.0 no
C224 . C225 . C226 . 115.6(5) yes
C224 . C225 . H2251 . 121.7 no
C226 . C225 . H2251 . 122.6 no
C225 . C226 . N221 . 126.3(5) yes
C225 . C226 . H2261 . 119.8 no
N221 . C226 . H2261 . 113.9 no
H2311 . O231 . H2312 . 114(4) no
C2 . N1 . C5 . 105.84(17) yes
N1 . C2 . C3 . 110.29(19) yes
N1 . C2 . C24 . 125.4(2) yes
C3 . C2 . C24 . 124.2(2) yes
C2 . C3 . C4 . 106.7(2) yes
C2 . C3 . H31 . 126.4 no
C4 . C3 . H31 . 126.9 no
C3 . C4 . C5 . 106.8(2) yes
C3 . C4 . H41 . 127.4 no
C5 . C4 . H41 . 125.8 no
C4 . C5 . N1 . 110.35(18) yes
C4 . C5 . C6 . 124.0(2) yes
N1 . C5 . C6 . 125.45(19) yes
C37 . C6 . C5 . 117.65(19) yes
C37 . C6 . C8 . 117.58(18) yes
C5 . C6 . C8 . 124.8(2) yes
C8 . N7 . C11 . 110.02(17) yes
C8 . N7 . H71 . 125.0(11) no
C11 . N7 . H71 . 124.8(11) no
C6 . C8 . N7 . 125.09(19) yes
C6 . C8 . C9 . 128.0(2) yes
N7 . C8 . C9 . 106.89(18) yes
C8 . C9 . C10 . 108.05(19) yes
C8 . C9 . H91 . 125.8 no
C10 . C9 . H91 . 126.2 no
C9 . C10 . C11 . 108.15(19) yes
C9 . C10 . H101 . 126.0 no
C11 . C10 . H101 . 125.8 no
C10 . C11 . N7 . 106.69(18) yes
C10 . C11 . C12 . 127.31(19) yes
N7 . C11 . C12 . 125.86(19) yes
C47 . C12 . C11 . 117.23(19) yes
C47 . C12 . C14 . 117.91(19) yes
C11 . C12 . C14 . 124.81(19) yes
C14 . N13 . C17 . 105.39(17) yes
C12 . C14 . N13 . 125.01(19) yes
C12 . C14 . C15 . 124.1(2) yes
N13 . C14 . C15 . 110.68(18) yes
C14 . C15 . C16 . 106.70(19) yes
C14 . C15 . H151 . 125.9 no
C16 . C15 . H151 . 127.4 no
C15 . C16 . C17 . 106.68(19) yes
C15 . C16 . H161 . 127.3 no
C17 . C16 . H161 . 126.0 no
C16 . C17 . N13 . 110.38(18) yes
C16 . C17 . C18 . 124.4(2) yes
N13 . C17 . C18 . 125.05(19) yes
C57 . C18 . C17 . 118.57(19) yes
C57 . C18 . C20 . 116.94(19) yes
C17 . C18 . C20 . 124.5(2) yes
C20 . N19 . C23 . 110.16(18) yes
C20 . N19 . H191 . 124.9(11) no
C23 . N19 . H191 . 124.9(11) no
C18 . C20 . N19 . 126.2(2) yes
C18 . C20 . C21 . 127.0(2) yes
N19 . C20 . C21 . 106.81(19) yes
C20 . C21 . C22 . 108.0(2) yes
C20 . C21 . H211 . 126.4 no
C22 . C21 . H211 . 125.6 no
C21 . C22 . C23 . 108.3(2) yes
C21 . C22 . H221 . 125.4 no
C23 . C22 . H221 . 126.3 no
C22 . C23 . N19 . 106.63(19) yes
C22 . C23 . C24 . 127.5(2) yes
N19 . C23 . C24 . 125.9(2) yes
C67 . C24 . C2 . 118.4(2) yes
C67 . C24 . C23 . 116.46(19) yes
C2 . C24 . C23 . 125.1(2) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C36 . H361 . N13 2_756 140.10(6) 0.928 2.491 3.258(4) yes
C58 . H581 . O31 2_756 139.38(6) 0.932 2.522 3.286(4) yes
C108 . H1081 . O31 1_455 140.78(7) 0.935 2.316 3.098(4) yes
C128 . H1281 . O61 1_454 157.53(6) 0.934 2.446 3.329(4) yes
C132 . H1321 . O231 . 164.14(8) 0.939 2.337 3.251(4) yes
N122 . H1221 . O61 1_454 162(2) 0.863 2.005 2.836(4) yes
N122 . H1222 . O41 2_655 177(2) 0.853 1.985 2.836(4) yes
N121 . H1212 . O42 2_655 164(2) 0.868 1.944 2.790(4) yes
N101 . H1011 . O61 1_454 158(3) 0.864 1.982 2.804(4) yes
N125 . H1252 . O32 2_766 179(3) 0.865 1.905 2.770(4) yes
N101 . H1012 . N201 1_455 172(2) 0.887 1.939 2.820(4) yes
N121 . H1211 . O231 . 166.9(20) 0.860 2.019 2.863(4) yes
N105 . H1052 . O51 1_665 151.2(19) 0.869 1.985 2.779(4) yes
N124 . H1242 . O52 2_556 170.6(20) 0.868 1.870 2.731(4) yes
N104 . H1042 . O51 1_665 146.5(18) 0.872 2.100 2.868(4) yes
N125 . H1251 . O51 2_556 145(2) 0.857 2.497 3.234(4) yes
N124 . H1241 . O62 1_454 165.3(20) 0.854 1.970 2.804(4) yes
N102 . H1021 . O31 1_455 160(2) 0.863 2.221 3.049(4) yes
N102 . H1022 . O52 2_556 131(2) 0.874 2.265 2.912(4) yes
N105 . H1051 . N211 2_766 159.8(20) 0.863 2.078 2.904(4) yes
O231 . H2311 . O42 1_565 173(4) 0.833 1.946 2.775(4) yes
O231 . H2312 . N221 2_665 175(4) 0.816 1.972 2.786(4) yes
N7 . H71 . N13 . 120.8(14) 0.847 2.380 2.906(4) yes
N19 . H191 . N1 . 121.2(14) 0.848 2.383 2.914(4) yes
N19 . H191 . N13 . 120.2(14) 0.848 2.378 2.899(4) yes
N104 . H1041 . O31 1_455 172(2) 0.872 2.010 2.877(4) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 03/03/17 at  9:52: 2
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (  101 ,X'S,U'S)  UNTIL C    (   24 ) 
CONT H    ( 1221 ,X'S)  UNTIL H    ( 1051 ) 
CONT H    ( 2311 ,X'S)  UNTIL H    ( 1041 ) 
RIDE C   ( 108,X'S) H   (1081,X'S) 
RIDE C   ( 110,X'S) H   (1101,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) 
RIDE C   ( 213,X'S) H   (2131,X'S) 
RIDE C   ( 214,X'S) H   (2141,X'S) 
RIDE C   ( 215,X'S) H   (2151,X'S) 
RIDE C   ( 216,X'S) H   (2161,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
RIDE C   ( 128,X'S) H   (1281,X'S) 
RIDE C   ( 130,X'S) H   (1301,X'S) 
RIDE C   ( 131,X'S) H   (1311,X'S) 
RIDE C   ( 132,X'S) H   (1321,X'S) 
RIDE C   ( 202,X'S) H   (2021,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) 
RIDE C   ( 204,X'S) H   (2041,X'S) 
RIDE C   ( 205,X'S) H   (2051,X'S) 
RIDE C   ( 206,X'S) H   (2061,X'S) 
RIDE C   ( 222,X'S) H   (2221,X'S) 
RIDE C   ( 223,X'S) H   (2231,X'S) 
RIDE C   ( 224,X'S) H   (2241,X'S) 
RIDE C   ( 225,X'S) H   (2251,X'S) 
RIDE C   ( 226,X'S) H   (2261,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
END            
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 03/03/17 at  9:52: 2
#
#LIST     16                                                                    
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 101) TO H(1011) 
CONT N ( 101) TO H(1012) 
REST 0.038, 0.002 = H(1011,U[ISO]) 
REST 0.038, 0.002 = H(1012,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(103) TO N ( 101) TO H(1011) 
CONT C(103) TO N ( 101) TO H(1012) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 102) TO H(1021) 
CONT N ( 102) TO H(1022) 
REST 0.035, 0.002 = H(1021,U[ISO]) 
REST 0.035, 0.002 = H(1022,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(103) TO N ( 102) TO H(1021) 
CONT C(103) TO N ( 102) TO H(1022) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 104) TO H(1042) 
CONT N ( 104) TO H(1041) 
REST 0.030, 0.002 = H(1042,U[ISO]) 
REST 0.030, 0.002 = H(1041,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(106) TO N ( 104) TO H(1042) 
CONT C(106) TO N ( 104) TO H(1041) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 105) TO H(1052) 
CONT N ( 105) TO H(1051) 
REST 0.033, 0.002 = H(1052,U[ISO]) 
REST 0.033, 0.002 = H(1051,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(106) TO N ( 105) TO H(1052) 
CONT C(106) TO N ( 105) TO H(1051) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 121) TO H(1212) 
CONT N ( 121) TO H(1211) 
REST 0.037, 0.002 = H(1212,U[ISO]) 
REST 0.037, 0.002 = H(1211,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(123) TO N ( 121) TO H(1212) 
CONT C(123) TO N ( 121) TO H(1211) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 122) TO H(1221) 
CONT N ( 122) TO H(1222) 
REST 0.034, 0.002 = H(1221,U[ISO]) 
REST 0.034, 0.002 = H(1222,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(123) TO N ( 122) TO H(1221) 
CONT C(123) TO N ( 122) TO H(1222) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 124) TO H(1242) 
CONT N ( 124) TO H(1241) 
REST 0.037, 0.002 = H(1242,U[ISO]) 
REST 0.037, 0.002 = H(1241,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(126) TO N ( 124) TO H(1242) 
CONT C(126) TO N ( 124) TO H(1241) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 125) TO H(1252) 
CONT N ( 125) TO H(1251) 
REST 0.032, 0.002 = H(1252,U[ISO]) 
REST 0.032, 0.002 = H(1251,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(126) TO N ( 125) TO H(1252) 
CONT C(126) TO N ( 125) TO H(1251) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 231) TO H(2311) 
CONT O ( 231) TO H(2312) 
REST 0.063, 0.002 = H(2311,U[ISO]) 
REST 0.063, 0.002 = H(2312,U[ISO]) 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 7) TO H(71) 
REST 0.023, 0.002 = H(71,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(71) TO N ( 7) TO C(8) 
CONT H(71) TO N ( 7) TO C(11) 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 19) TO H(191) 
REST 0.025, 0.002 = H(191,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(191) TO N ( 19) TO C(20) 
CONT H(191) TO N ( 19) TO C(23) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 -4 2 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_5
_database_code_depnum_ccdc_archive 'CCDC 1574947'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_DIFMN02_2_5                 
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: Two benzoate groups and one bis-amidinium molecule were poorly behaved, 
and so it was necessary to add restraints to the bond lengths as well as the 
thermal and vibrational ellipsoid parameters of these groups in 
order to achieve a sensible refinement. Residual electron density is located
around these groups.
;
_vrf_PLAT097_2_5                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.72 eA-3  
RESPONSE: Two benzoate groups and one bis-amidinium molecule were poorly behaved, 
and so it was necessary to add restraints to the bond lengths as well as the 
thermal and vibrational ellipsoid parameters of these groups in 
order to achieve a sensible refinement. Residual electron density is located
around these groups.
;
_vrf_PLAT098_2_5                 
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -0.88 eA-3  
RESPONSE: Two benzoate groups and one bis-amidinium molecule were poorly behaved, 
and so it was necessary to add restraints to the bond lengths as well as the 
thermal and vibrational ellipsoid parameters of these groups in 
order to achieve a sensible refinement. Residual electron density is located
around these groups.
;
_vrf_PLAT213_2_5                 
;
PROBLEM: Atom O51             has ADP max/min Ratio .....        4.2 prolat
RESPONSE: Two benzoate groups and one bis-amidinium molecule were poorly behaved, 
and so it was necessary to add restraints to the bond lengths as well as the 
thermal and vibrational ellipsoid parameters of these groups in 
order to achieve a sensible refinement. Residual electron density is located
around these groups.
;
# end Validation Reply Form

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.081 0.419 1.081 2106 625 ' '
2 0.079 0.947 0.689 9 8 ' '
3 0.921 0.053 0.311 8 6 ' '
_platon_squeeze_details          
;
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
;The asymmetric unit cell contains one and a half porphyrin molecules and a 
total of three bis-amidinium molecules (made up of two complete bis-amidiniums
and two half-amidiniums located about special positions.

Two benzoate groups and one bis-amidinium molecule were poorly behaved, and so
it was necessary to add restraints to the bond lengths as well as the thermal
and vibrational ellipsoid parameters of these groups in 
order to achieve a sensible refinement. Residual electron density is located
around these groups.

Areas of diffuse electron density, believed to result from disordered pyridine 
and water solvents were present, which could not be sensibly refined, and so 
PLATON-SQUEEZE was used to include this electron density in the refinement.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H  hydrogen 
atoms were generally visible in the Fourier differnence map and
were refined with restraints on bond lengths and angles.,SQUEEZE
;

_cell_length_a                   15.6606(3)
_cell_length_b                   18.9312(3)
_cell_length_c                   20.4250(3)
_cell_angle_alpha                86.1854(13)
_cell_angle_beta                 79.7696(15)
_cell_angle_gamma                72.5303(15)
_cell_volume                     5683.78(8)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C96 H75 N18 O12'
_chemical_formula_moiety         '1.5(C48 H26 N4 O8), 3(C8 H12 N4)'
_chemical_compound_source        synthesized
_chemical_formula_weight         1672.76

_cell_measurement_reflns_used    25303
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      73.7
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.37

_exptl_crystal_density_diffrn    0.977
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1746
_exptl_absorpt_coefficient_mu    0.543

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            118047
_reflns_number_total             22953
_diffrn_reflns_av_R_equivalents  0.043

_diffrn_reflns_theta_min         2.447
_diffrn_reflns_theta_max         74.181
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        72.698
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -19
_reflns_limit_h_max              19
_reflns_limit_k_min              -23
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   2.44
_oxford_diffrn_Wilson_scale      0.63

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.88
_refine_diff_density_max         2.72

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         22854
_refine_ls_number_restraints     287
_refine_ls_number_parameters     1216
_oxford_refine_ls_R_factor_ref   0.0929
_refine_ls_wR_factor_ref         0.2245
_refine_ls_goodness_of_fit_ref   0.9274
_refine_ls_shift/su_max          0.0003973
_refine_ls_shift/su_mean         0.0000410

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        22859
_refine_ls_R_factor_all          0.0929
_refine_ls_wR_factor_all         0.2250

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                18002
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_gt          0.2042

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 908. 0.151E+04 888. 349. 73.2 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N101 N 0.40595(15) 0.44931(12) -0.01288(10) 0.0228 1.0000 Uani . . . . . .
C102 C 0.36806(19) 0.40728(14) 0.03351(12) 0.0235 1.0000 Uani . . . . . .
C103 C 0.2967(2) 0.38819(16) 0.00896(14) 0.0303 1.0000 Uani . . . . . .
C104 C 0.2932(2) 0.41833(17) -0.05268(14) 0.0311 1.0000 Uani . . . . . .
C105 C 0.36076(19) 0.45736(15) -0.06572(12) 0.0251 1.0000 Uani . . . . . .
C106 C 0.39309(18) 0.38545(14) 0.09637(12) 0.0228 1.0000 Uani . . . . . .
N107 N 0.51193(15) 0.44838(12) 0.09251(10) 0.0223 1.0000 Uani D . . . . .
C108 C 0.56907(18) 0.45484(15) 0.13428(12) 0.0239 1.0000 Uani D . . . . .
C109 C 0.5546(2) 0.40997(15) 0.19231(13) 0.0283 1.0000 Uani . . . . . .
C110 C 0.4896(2) 0.37936(15) 0.18491(12) 0.0263 1.0000 Uani . . . . . .
C111 C 0.46100(19) 0.40389(14) 0.12186(12) 0.0227 1.0000 Uani D . . . . .
C112 C 0.62704(19) 0.49956(15) 0.12355(12) 0.0254 1.0000 Uani . U . . . .
O131 O 0.1687(2) 0.17038(16) 0.25385(12) 0.0606 1.0000 Uani . . . . . .
O132 O 0.19422(19) 0.22379(14) 0.33785(10) 0.0460 1.0000 Uani . . . . . .
C133 C 0.2007(2) 0.21410(16) 0.27700(14) 0.0353 1.0000 Uani . . . . . .
C134 C 0.2488(2) 0.25863(15) 0.22901(13) 0.0281 1.0000 Uani . . . . . .
C135 C 0.2903(2) 0.23257(15) 0.16546(13) 0.0276 1.0000 Uani . . . . . .
C136 C 0.33718(19) 0.27336(14) 0.12253(12) 0.0245 1.0000 Uani . . . . . .
C137 C 0.34145(18) 0.34142(14) 0.14109(12) 0.0235 1.0000 Uani . . . . . .
C138 C 0.2965(2) 0.36861(15) 0.20410(13) 0.0276 1.0000 Uani . . . . . .
C139 C 0.2526(2) 0.32671(15) 0.24759(13) 0.0309 1.0000 Uani . . . . . .
O141 O 0.81411(17) 0.47808(16) 0.38618(14) 0.0556 1.0000 Uani D U . . . .
O142 O 0.7883(2) 0.59934(16) 0.36357(15) 0.0626 1.0000 Uani D U . . . .
C143 C 0.7894(2) 0.53502(18) 0.35230(17) 0.0479 1.0000 Uani D U . . . .
C144 C 0.7545(2) 0.5230(2) 0.28991(16) 0.0543 1.0000 Uani D U . . . .
C145 C 0.7778(2) 0.4556(2) 0.25754(16) 0.0494 1.0000 Uani D U . . . .
C146 C 0.7403(2) 0.4457(2) 0.20168(15) 0.0453 1.0000 Uani D U . . . .
C147 C 0.67508(18) 0.50542(16) 0.17897(13) 0.0320 1.0000 Uani D U . . . .
C148 C 0.6541(2) 0.5732(2) 0.21055(14) 0.0412 1.0000 Uani D U . . . .
C149 C 0.6927(2) 0.5827(2) 0.26430(15) 0.0479 1.0000 Uani D U . . . .
N201 N 0.4931(3) 0.2548(2) 0.5175(2) 0.0685 1.0000 Uani D . . . . .
N202 N 0.6313(2) 0.26612(18) 0.5283(2) 0.0603 1.0000 Uani D . . . . .
C203 C 0.5440(3) 0.2936(2) 0.5340(2) 0.0538 1.0000 Uani D . . . . .
N204 N 0.2984(2) 0.6292(2) 0.61210(16) 0.0553 1.0000 Uani D . . . . .
N205 N 0.4369(3) 0.63549(19) 0.6295(2) 0.0593 1.0000 Uani D . . . . .
C206 C 0.3854(2) 0.5978(2) 0.61327(16) 0.0418 1.0000 Uani D . . . . .
C207 C 0.5000(2) 0.37128(19) 0.5581(2) 0.0466 1.0000 Uani . . . . . .
C208 C 0.4294(2) 0.41758(19) 0.5283(2) 0.0441 1.0000 Uani . . . . . .
C209 C 0.3932(2) 0.49109(18) 0.54656(16) 0.0347 1.0000 Uani . . . . . .
C210 C 0.4248(2) 0.51953(18) 0.59568(15) 0.0350 1.0000 Uani . . . . . .
C211 C 0.4943(2) 0.4731(2) 0.62690(18) 0.0432 1.0000 Uani . . . . . .
C212 C 0.5310(2) 0.4000(2) 0.6086(2) 0.0479 1.0000 Uani . . . . . .
N221 N -0.05982(17) 0.21951(13) 0.60728(11) 0.0264 1.0000 Uani D . . . . .
N222 N -0.01561(18) 0.26490(14) 0.69269(12) 0.0307 1.0000 Uani D . . . . .
C223 C -0.02142(17) 0.26351(14) 0.62934(13) 0.0235 1.0000 Uani D . . . . .
N224 N 0.14357(16) 0.44715(12) 0.38592(11) 0.0268 1.0000 Uani D . . . . .
N225 N 0.17646(16) 0.49615(13) 0.47478(12) 0.0274 1.0000 Uani D . . . . .
C226 C 0.14162(17) 0.45110(14) 0.45036(13) 0.0231 1.0000 Uani D . . . . .
C227 C 0.01860(17) 0.31274(15) 0.58214(13) 0.0237 1.0000 Uani . . . . . .
C228 C 0.0619(2) 0.28767(16) 0.51855(15) 0.0341 1.0000 Uani . . . . . .
C229 C 0.1007(2) 0.33335(16) 0.47488(15) 0.0341 1.0000 Uani . . . . . .
C230 C 0.09751(17) 0.40298(14) 0.49593(13) 0.0231 1.0000 Uani . . . . . .
C231 C 0.05363(17) 0.42770(14) 0.55909(12) 0.0205 1.0000 Uani . . . . . .
C232 C 0.01316(17) 0.38280(14) 0.60218(12) 0.0215 1.0000 Uani . . . . . .
N241 N 0.06964(16) 0.09579(13) 0.34647(10) 0.0257 1.0000 Uani D . . . . .
N242 N 0.15159(16) 0.11065(14) 0.42420(11) 0.0272 1.0000 Uani D . . . . .
C243 C 0.09144(17) 0.08391(13) 0.40652(12) 0.0213 1.0000 Uani D . . . . .
C244 C 0.04485(17) 0.03996(13) 0.45460(12) 0.0202 1.0000 Uani . . . . . .
C245 C 0.01849(18) -0.01683(14) 0.43266(12) 0.0221 1.0000 Uani . . . . . .
C246 C 0.02674(19) 0.05664(14) 0.52204(12) 0.0243 1.0000 Uani . . . . . .
N261 N -0.0562(3) 1.0260(3) 0.1796(2) 0.1031 1.0000 Uani D U . . . .
N262 N -0.0206(3) 1.1295(3) 0.1300(3) 0.1212 1.0000 Uani D U . . . .
C263 C -0.0311(3) 1.0634(3) 0.1273(2) 0.0910 1.0000 Uani D U . . . .
C264 C -0.0151(3) 1.0306(2) 0.0608(2) 0.0716 1.0000 Uani D U . . . .
C265 C 0.0254(3) 0.9540(3) 0.0553(2) 0.0743 1.0000 Uani D U . . . .
C266 C -0.0414(3) 1.0773(3) 0.0072(2) 0.0743 1.0000 Uani D U . . . .
N1 N 0.54980(14) 0.83159(12) 0.14257(10) 0.0215 1.0000 Uani . . . . . .
C2 C 0.58790(18) 0.85332(15) 0.19010(13) 0.0244 1.0000 Uani . . . . . .
C3 C 0.5577(2) 0.82562(18) 0.25566(14) 0.0337 1.0000 Uani . . . . . .
C4 C 0.5038(2) 0.78485(18) 0.24611(14) 0.0340 1.0000 Uani . . . . . .
C5 C 0.49816(18) 0.78920(14) 0.17560(13) 0.0234 1.0000 Uani . . . . . .
C6 C 0.45007(17) 0.75172(14) 0.14629(13) 0.0225 1.0000 Uani . . . . . .
N7 N 0.47491(15) 0.80131(12) 0.03120(10) 0.0213 1.0000 Uani D . . . . .
C8 C 0.44298(17) 0.75560(14) 0.07842(12) 0.0219 1.0000 Uani D . . . . .
C9 C 0.39514(19) 0.71886(15) 0.04558(13) 0.0268 1.0000 Uani . . . . . .
C10 C 0.39723(19) 0.74411(15) -0.01872(14) 0.0269 1.0000 Uani . . . . . .
C11 C 0.44492(17) 0.79858(14) -0.02771(12) 0.0228 1.0000 Uani D . . . . .
C12 C 0.45556(18) 0.84306(14) -0.08468(12) 0.0227 1.0000 Uani . U . . . .
N13 N 0.56011(14) 0.90206(12) -0.04936(10) 0.0210 1.0000 Uani . . . . . .
C14 C 0.50723(17) 0.89291(14) -0.09278(12) 0.0206 1.0000 Uani . . . . . .
C15 C 0.51448(18) 0.94028(14) -0.15184(12) 0.0233 1.0000 Uani . . . . . .
C16 C 0.57440(18) 0.97636(14) -0.14395(12) 0.0232 1.0000 Uani . . . . . .
C17 C 0.60378(17) 0.95108(14) -0.08005(12) 0.0206 1.0000 Uani . . . . . .
C18 C 0.66987(17) 0.97364(14) -0.05590(12) 0.0205 1.0000 Uani . . . . . .
N19 N 0.64356(15) 0.92755(12) 0.05954(10) 0.0210 1.0000 Uani D . . . . .
C20 C 0.68993(17) 0.95915(14) 0.00846(12) 0.0213 1.0000 Uani D . . . . .
C21 C 0.76167(19) 0.97387(16) 0.03430(13) 0.0271 1.0000 Uani . . . . . .
C22 C 0.75583(19) 0.95276(16) 0.09964(14) 0.0285 1.0000 Uani . . . . . .
C23 C 0.68041(18) 0.92329(14) 0.11633(12) 0.0221 1.0000 Uani D . . . . .
C24 C 0.65143(18) 0.89389(14) 0.17787(12) 0.0222 1.0000 Uani . . . . . .
O31 O 0.7862(2) 0.90844(15) 0.45692(11) 0.0497 1.0000 Uani . . . . . .
O32 O 0.79519(19) 1.01791(14) 0.41407(12) 0.0464 1.0000 Uani . . . . . .
C33 C 0.7815(2) 0.95649(18) 0.41094(15) 0.0356 1.0000 Uani . . . . . .
C34 C 0.7552(2) 0.93880(16) 0.34762(14) 0.0300 1.0000 Uani . . . . . .
C35 C 0.7640(2) 0.86618(16) 0.33211(14) 0.0311 1.0000 Uani . . . . . .
C36 C 0.7336(2) 0.85077(16) 0.27607(14) 0.0290 1.0000 Uani . . . . . .
C37 C 0.69141(18) 0.90832(15) 0.23536(12) 0.0239 1.0000 Uani . . . . . .
C38 C 0.6856(2) 0.98072(15) 0.25019(13) 0.0277 1.0000 Uani . . . . . .
C39 C 0.7179(2) 0.99544(16) 0.30538(14) 0.0295 1.0000 Uani . . . . . .
O41 O 0.90879(14) 1.17652(11) -0.21530(10) 0.0320 1.0000 Uani . . . . . .
O42 O 0.88819(16) 1.11910(12) -0.30007(10) 0.0377 1.0000 Uani . . . . . .
C43 C 0.87757(18) 1.13201(14) -0.23899(13) 0.0248 1.0000 Uani . . . . . .
C44 C 0.82393(17) 1.09086(14) -0.19117(12) 0.0218 1.0000 Uani . U . . . .
C45 C 0.78041(18) 1.12029(14) -0.12935(12) 0.0222 1.0000 Uani . . . . . .
C46 C 0.73006(18) 1.08254(14) -0.08560(12) 0.0223 1.0000 Uani . . . . . .
C47 C 0.72396(17) 1.01420(14) -0.10226(12) 0.0213 1.0000 Uani . U . . . .
C48 C 0.76952(19) 0.98425(14) -0.16400(13) 0.0255 1.0000 Uani . U . . . .
C49 C 0.81775(19) 1.02276(15) -0.20840(13) 0.0258 1.0000 Uani . U . . . .
O51 O 0.3167(4) 0.7770(2) -0.3482(2) 0.1605 1.0000 Uani D U . . . .
O52 O 0.1934(3) 0.7904(2) -0.2744(3) 0.1534 1.0000 Uani D U . . . .
C53 C 0.2745(3) 0.7904(2) -0.2903(2) 0.1134 1.0000 Uani D U . . . .
C54 C 0.3231(3) 0.80792(19) -0.2402(2) 0.0670 1.0000 Uani D U . . . .
C55 C 0.4160(3) 0.80061(18) -0.25304(18) 0.0569 1.0000 Uani D U . . . .
C56 C 0.4598(2) 0.81248(16) -0.20285(13) 0.0361 1.0000 Uani D U . . . .
C57 C 0.40971(18) 0.83356(15) -0.13972(13) 0.0294 1.0000 Uani D U . . . .
C58 C 0.3162(2) 0.84399(19) -0.12834(19) 0.0449 1.0000 Uani D U . . . .
C59 C 0.2733(3) 0.8299(2) -0.1777(2) 0.0624 1.0000 Uani D U . . . .
O61 O 0.26461(17) 0.50814(12) 0.29870(11) 0.0412 1.0000 Uani . . . . . .
O62 O 0.20681(14) 0.60003(11) 0.37030(9) 0.0291 1.0000 Uani . . . . . .
C63 C 0.25528(18) 0.57249(14) 0.31668(13) 0.0238 1.0000 Uani . . . . . .
C64 C 0.30402(17) 0.61962(14) 0.27188(12) 0.0216 1.0000 Uani . . . . . .
C65 C 0.36980(19) 0.58777(14) 0.21850(13) 0.0258 1.0000 Uani . . . . . .
C66 C 0.41731(18) 0.63053(15) 0.17791(13) 0.0267 1.0000 Uani . . . . . .
C67 C 0.39919(17) 0.70572(14) 0.18969(12) 0.0216 1.0000 Uani . . . . . .
C68 C 0.33204(17) 0.73738(14) 0.24290(13) 0.0219 1.0000 Uani . . . . . .
C69 C 0.28535(17) 0.69495(14) 0.28400(12) 0.0224 1.0000 Uani . . . . . .
H1031 H 0.2584 0.3614 0.0307 0.0381 1.0000 Uiso R . . . . .
H1041 H 0.2545 0.4112 -0.0814 0.0371 1.0000 Uiso R . . . . .
H1091 H 0.5874 0.4033 0.2288 0.0347 1.0000 Uiso R . . . . .
H1101 H 0.4696 0.3474 0.2141 0.0340 1.0000 Uiso R . . . . .
H1351 H 0.2851 0.1867 0.1536 0.0349 1.0000 Uiso R . . . . .
H1361 H 0.3674 0.2550 0.0788 0.0311 1.0000 Uiso R . . . . .
H1381 H 0.2942 0.4156 0.2173 0.0353 1.0000 Uiso R . . . . .
H1391 H 0.2263 0.3434 0.2911 0.0377 1.0000 Uiso R . . . . .
H1451 H 0.8201 0.4134 0.2702 0.0597 1.0000 Uiso R . . . . .
H1461 H 0.7555 0.3992 0.1815 0.0547 1.0000 Uiso R . . . . .
H1481 H 0.6120 0.6159 0.1938 0.0520 1.0000 Uiso R . . . . .
H1491 H 0.6798 0.6311 0.2843 0.0602 1.0000 Uiso R . . . . .
H2081 H 0.4039 0.3986 0.4960 0.0543 1.0000 Uiso R . . . . .
H2091 H 0.3483 0.5230 0.5263 0.0416 1.0000 Uiso R . . . . .
H2111 H 0.5154 0.4924 0.6599 0.0538 1.0000 Uiso R . . . . .
H2121 H 0.5758 0.3686 0.6302 0.0592 1.0000 Uiso R . . . . .
H2281 H 0.0661 0.2399 0.5038 0.0418 1.0000 Uiso R . . . . .
H2291 H 0.1292 0.3171 0.4326 0.0405 1.0000 Uiso R . . . . .
H2311 H 0.0538 0.4756 0.5713 0.0264 1.0000 Uiso R . . . . .
H2321 H -0.0175 0.4001 0.6454 0.0276 1.0000 Uiso R . . . . .
H2451 H 0.0325 -0.0282 0.3869 0.0291 1.0000 Uiso R . . . . .
H2461 H 0.0444 0.0956 0.5379 0.0309 1.0000 Uiso R . . . . .
H2651 H 0.0422 0.9245 0.0920 0.0944 1.0000 Uiso R . . . . .
H2661 H -0.0693 1.1291 0.0147 0.0916 1.0000 Uiso R . . . . .
H31 H 0.5754 0.8326 0.2961 0.0424 1.0000 Uiso R . . . . .
H41 H 0.4744 0.7565 0.2799 0.0421 1.0000 Uiso R . . . . .
H91 H 0.3682 0.6819 0.0650 0.0339 1.0000 Uiso R . . . . .
H101 H 0.3740 0.7296 -0.0519 0.0345 1.0000 Uiso R . . . . .
H151 H 0.4825 0.9440 -0.1884 0.0307 1.0000 Uiso R . . . . .
H161 H 0.5977 1.0105 -0.1751 0.0298 1.0000 Uiso R . . . . .
H211 H 0.8045 0.9967 0.0103 0.0356 1.0000 Uiso R . . . . .
H221 H 0.7932 0.9553 0.1298 0.0372 1.0000 Uiso R . . . . .
H351 H 0.7915 0.8276 0.3602 0.0397 1.0000 Uiso R . . . . .
H361 H 0.7443 0.8003 0.2654 0.0374 1.0000 Uiso R . . . . .
H381 H 0.6586 1.0184 0.2217 0.0360 1.0000 Uiso R . . . . .
H391 H 0.7134 1.0454 0.3140 0.0376 1.0000 Uiso R . . . . .
H451 H 0.7824 1.1660 -0.1166 0.0282 1.0000 Uiso R . . . . .
H461 H 0.6992 1.1039 -0.0434 0.0287 1.0000 Uiso R . . . . .
H481 H 0.7678 0.9364 -0.1756 0.0326 1.0000 Uiso R . . . . .
H491 H 0.8484 1.0033 -0.2509 0.0322 1.0000 Uiso R . . . . .
H551 H 0.4489 0.7889 -0.2949 0.0699 1.0000 Uiso R . . . . .
H561 H 0.5239 0.8079 -0.2116 0.0453 1.0000 Uiso R . . . . .
H581 H 0.2818 0.8614 -0.0852 0.0568 1.0000 Uiso R . . . . .
H591 H 0.2108 0.8352 -0.1693 0.0772 1.0000 Uiso R . . . . .
H651 H 0.3846 0.5352 0.2085 0.0335 1.0000 Uiso R . . . . .
H661 H 0.4642 0.6086 0.1419 0.0335 1.0000 Uiso R . . . . .
H681 H 0.3183 0.7885 0.2506 0.0271 1.0000 Uiso R . . . . .
H691 H 0.2394 0.7180 0.3202 0.0285 1.0000 Uiso R . . . . .
H2251 H 0.198(2) 0.5267(16) 0.4476(11) 0.0347 1.0000 Uiso D . . . . .
H2221 H 0.017(2) 0.2909(18) 0.7047(12) 0.0393 1.0000 Uiso D . . . . .
H71 H 0.5090(19) 0.8283(15) 0.0373(10) 0.0266 1.0000 Uiso D . . . . .
H2252 H 0.176(2) 0.4974(17) 0.5168(9) 0.0350 1.0000 Uiso D . . . . .
H2241 H 0.1084(19) 0.4257(18) 0.3724(11) 0.0318 1.0000 Uiso D . . . . .
H2412 H 0.0241(18) 0.0817(18) 0.3384(12) 0.0328 1.0000 Uiso D . . . . .
H2222 H -0.037(2) 0.2355(17) 0.7205(11) 0.0395 1.0000 Uiso D . . . . .
H2422 H 0.176(2) 0.1390(17) 0.3969(12) 0.0353 1.0000 Uiso D . . . . .
H191 H 0.6000(18) 0.9091(17) 0.0556(10) 0.0291 1.0000 Uiso D . . . . .
H2242 H 0.173(2) 0.4722(17) 0.3585(11) 0.0325 1.0000 Uiso D . . . . .
H2212 H -0.065(2) 0.2203(17) 0.5653(10) 0.0345 1.0000 Uiso D . . . . .
H2421 H 0.171(2) 0.0977(17) 0.4621(12) 0.0356 1.0000 Uiso D . . . . .
H2411 H 0.094(2) 0.1240(17) 0.3188(11) 0.0331 1.0000 Uiso D . . . . .
H2211 H -0.078(2) 0.1872(15) 0.6340(11) 0.0344 1.0000 Uiso D . . . . .
H1071 H 0.5038(18) 0.4729(15) 0.0566(12) 0.0307 1.0000 Uiso D . . . . .
H2611 H -0.063(5) 1.045(2) 0.2190(11) 0.1222 1.0000 Uiso D . . . . .
H2612 H -0.065(5) 0.982(2) 0.1768(15) 0.1222 1.0000 Uiso D . . . . .
H2621 H -0.026(6) 1.150(2) 0.1684(12) 0.1383 1.0000 Uiso D . . . . .
H2622 H 0.028(3) 1.140(2) 0.109(3) 0.1383 1.0000 Uiso D . . . . .
H2011 H 0.5184(18) 0.2088(16) 0.501(3) 0.0811 1.0000 Uiso D . . . . .
H2012 H 0.444(2) 0.257(3) 0.5469(17) 0.0811 1.0000 Uiso D . . . . .
H2021 H 0.6662(17) 0.2933(15) 0.536(2) 0.0710 1.0000 Uiso D . . . . .
H2022 H 0.6566(17) 0.2194(13) 0.517(2) 0.0710 1.0000 Uiso D . . . . .
H2041 H 0.2781(18) 0.6771(11) 0.615(2) 0.0680 1.0000 Uiso D . . . . .
H2042 H 0.2653(18) 0.6048(16) 0.600(2) 0.0680 1.0000 Uiso D . . . . .
H2051 H 0.418(2) 0.6832(11) 0.630(3) 0.0720 1.0000 Uiso D . . . . .
H2052 H 0.4948(15) 0.6137(16) 0.628(2) 0.0720 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.380(5)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N101 . C102 . 1.366(3) yes
N101 . C105 . 1.369(3) yes
C102 . C103 . 1.448(4) yes
C102 . C106 . 1.408(4) yes
C103 . C104 . 1.350(4) yes
C103 . H1031 . 0.933 no
C104 . C105 . 1.443(4) yes
C104 . H1041 . 0.957 no
C105 . C112 2_665 1.408(3) yes
C106 . C111 . 1.403(4) yes
C106 . C137 . 1.492(3) yes
N107 . C108 . 1.376(3) yes
N107 . C111 . 1.368(3) yes
N107 . H1071 . 0.851(18) no
C108 . C109 . 1.436(3) yes
C108 . C112 . 1.398(4) yes
C109 . C110 . 1.348(4) yes
C109 . H1091 . 0.959 no
C110 . C111 . 1.440(3) yes
C110 . H1101 . 0.904 no
C112 . C147 . 1.493(3) yes
O131 . C133 . 1.243(4) yes
O132 . C133 . 1.250(4) yes
C133 . C134 . 1.500(3) yes
C134 . C135 . 1.394(4) yes
C134 . C139 . 1.388(4) yes
C135 . C136 . 1.388(3) yes
C135 . H1351 . 0.947 no
C136 . C137 . 1.391(4) yes
C136 . H1361 . 0.967 no
C137 . C138 . 1.402(4) yes
C138 . C139 . 1.381(4) yes
C138 . H1381 . 0.935 no
C139 . H1391 . 0.944 no
O141 . C143 . 1.239(3) yes
O142 . C143 . 1.249(3) yes
C143 . C144 . 1.528(4) yes
C144 . C145 . 1.396(4) yes
C144 . C149 . 1.390(4) yes
C145 . C146 . 1.419(3) yes
C145 . H1451 . 0.926 no
C146 . C147 . 1.394(3) yes
C146 . H1461 . 0.942 no
C147 . C148 . 1.397(3) yes
C148 . C149 . 1.390(3) yes
C148 . H1481 . 0.964 no
C149 . H1491 . 0.978 no
N201 . C203 . 1.330(5) yes
N201 . H2011 . 0.903(19) no
N201 . H2012 . 0.882(19) no
N202 . C203 . 1.295(5) yes
N202 . H2021 . 0.892(19) no
N202 . H2022 . 0.885(19) no
C203 . C207 . 1.500(5) yes
N204 . C206 . 1.316(5) yes
N204 . H2041 . 0.869(19) no
N204 . H2042 . 0.868(19) no
N205 . C206 . 1.319(5) yes
N205 . H2051 . 0.862(19) no
N205 . H2052 . 0.873(19) no
C206 . C210 . 1.466(5) yes
C207 . C208 . 1.395(5) yes
C207 . C212 . 1.417(5) yes
C208 . C209 . 1.385(5) yes
C208 . H2081 . 0.967 no
C209 . C210 . 1.396(5) yes
C209 . H2091 . 0.920 no
C210 . C211 . 1.400(4) yes
C211 . C212 . 1.379(5) yes
C211 . H2111 . 0.938 no
C212 . H2121 . 0.930 no
N221 . C223 . 1.306(3) yes
N221 . H2212 . 0.875(18) no
N221 . H2211 . 0.868(18) no
N222 . C223 . 1.316(4) yes
N222 . H2221 . 0.883(18) no
N222 . H2222 . 0.867(18) no
C223 . C227 . 1.486(3) yes
N224 . C226 . 1.318(4) yes
N224 . H2241 . 0.864(18) no
N224 . H2242 . 0.873(18) no
N225 . C226 . 1.306(3) yes
N225 . H2251 . 0.871(18) no
N225 . H2252 . 0.858(18) no
C226 . C230 . 1.487(3) yes
C227 . C228 . 1.396(4) yes
C227 . C232 . 1.388(4) yes
C228 . C229 . 1.390(4) yes
C228 . H2281 . 0.951 no
C229 . C230 . 1.397(4) yes
C229 . H2291 . 0.925 no
C230 . C231 . 1.388(4) yes
C231 . C232 . 1.387(3) yes
C231 . H2311 . 0.958 no
C232 . H2321 . 0.954 no
N241 . C243 . 1.318(3) yes
N241 . H2412 . 0.878(18) no
N241 . H2411 . 0.869(18) no
N242 . C243 . 1.306(3) yes
N242 . H2422 . 0.872(18) no
N242 . H2421 . 0.872(18) no
C243 . C244 . 1.480(3) yes
C244 . C245 . 1.387(4) yes
C244 . C246 . 1.394(3) yes
C245 . C246 2_556 1.386(3) yes
C245 . H2451 . 0.945 no
C246 . H2461 . 0.955 no
N261 . C263 . 1.309(4) yes
N261 . H2611 . 0.87(2) no
N261 . H2612 . 0.888(19) no
N262 . C263 . 1.317(4) yes
N262 . H2621 . 0.88(2) no
N262 . H2622 . 0.87(2) no
C263 . C264 . 1.480(4) yes
C264 . C265 . 1.400(4) yes
C264 . C266 . 1.401(4) yes
C265 . C266 2_575 1.394(3) yes
C265 . H2651 . 0.933 no
C266 . H2661 . 0.956 no
N1 . C2 . 1.369(3) yes
N1 . C5 . 1.370(3) yes
C2 . C3 . 1.457(3) yes
C2 . C24 . 1.410(3) yes
C3 . C4 . 1.348(4) yes
C3 . H31 . 0.945 no
C4 . C5 . 1.454(4) yes
C4 . H41 . 0.981 no
C5 . C6 . 1.402(4) yes
C6 . C8 . 1.405(4) yes
C6 . C67 . 1.497(3) yes
N7 . C8 . 1.381(3) yes
N7 . C11 . 1.377(3) yes
N7 . H71 . 0.871(17) no
C8 . C9 . 1.431(4) yes
C9 . C10 . 1.366(4) yes
C9 . H91 . 0.951 no
C10 . C11 . 1.429(3) yes
C10 . H101 . 0.916 no
C11 . C12 . 1.406(3) yes
C12 . C14 . 1.401(3) yes
C12 . C57 . 1.484(3) yes
N13 . C14 . 1.368(3) yes
N13 . C17 . 1.369(3) yes
C14 . C15 . 1.463(3) yes
C15 . C16 . 1.351(4) yes
C15 . H151 . 0.958 no
C16 . C17 . 1.464(3) yes
C16 . H161 . 0.980 no
C17 . C18 . 1.404(3) yes
C18 . C20 . 1.396(4) yes
C18 . C47 . 1.487(3) yes
N19 . C20 . 1.372(3) yes
N19 . C23 . 1.372(3) yes
N19 . H191 . 0.872(18) no
C20 . C21 . 1.427(4) yes
C21 . C22 . 1.363(4) yes
C21 . H211 . 0.952 no
C22 . C23 . 1.432(3) yes
C22 . H221 . 0.934 no
C23 . C24 . 1.397(3) yes
C24 . C37 . 1.500(3) yes
O31 . C33 . 1.259(4) yes
O32 . C33 . 1.252(4) yes
C33 . C34 . 1.511(4) yes
C34 . C35 . 1.392(4) yes
C34 . C39 . 1.384(4) yes
C35 . C36 . 1.394(4) yes
C35 . H351 . 0.944 no
C36 . C37 . 1.399(4) yes
C36 . H361 . 0.953 no
C37 . C38 . 1.396(4) yes
C38 . C39 . 1.390(4) yes
C38 . H381 . 0.937 no
C39 . H391 . 0.952 no
O41 . C43 . 1.252(3) yes
O42 . C43 . 1.259(3) yes
C43 . C44 . 1.506(3) yes
C44 . C45 . 1.389(4) yes
C44 . C49 . 1.394(4) yes
C45 . C46 . 1.391(3) yes
C45 . H451 . 0.932 no
C46 . C47 . 1.394(3) yes
C46 . H461 . 0.959 no
C47 . C48 . 1.398(4) yes
C48 . C49 . 1.387(3) yes
C48 . H481 . 0.960 no
C49 . H491 . 0.952 no
O51 . C53 . 1.249(4) yes
O52 . C53 . 1.253(4) yes
C53 . C54 . 1.488(3) yes
C54 . C55 . 1.397(4) yes
C54 . C59 . 1.391(4) yes
C55 . C56 . 1.394(3) yes
C55 . H551 . 0.920 no
C56 . C57 . 1.399(3) yes
C56 . H561 . 0.967 no
C57 . C58 . 1.396(3) yes
C58 . C59 . 1.387(4) yes
C58 . H581 . 0.969 no
C59 . H591 . 0.939 no
O61 . C63 . 1.254(3) yes
O62 . C63 . 1.261(3) yes
C63 . C64 . 1.506(3) yes
C64 . C65 . 1.389(4) yes
C64 . C69 . 1.397(4) yes
C65 . C66 . 1.396(3) yes
C65 . H651 . 0.979 no
C66 . C67 . 1.394(4) yes
C66 . H661 . 0.959 no
C67 . C68 . 1.396(4) yes
C68 . C69 . 1.389(3) yes
C68 . H681 . 0.943 no
C69 . H691 . 0.959 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C102 . N101 . C105 . 106.2(2) yes
N101 . C102 . C103 . 110.0(2) yes
N101 . C102 . C106 . 125.9(2) yes
C103 . C102 . C106 . 124.1(2) yes
C102 . C103 . C104 . 106.9(2) yes
C102 . C103 . H1031 . 128.3 no
C104 . C103 . H1031 . 124.8 no
C103 . C104 . C105 . 106.8(2) yes
C103 . C104 . H1041 . 124.1 no
C105 . C104 . H1041 . 129.1 no
C104 . C105 . C112 2_665 123.4(2) yes
C104 . C105 . N101 . 110.2(2) yes
C112 2_665 C105 . N101 . 126.3(2) yes
C102 . C106 . C111 . 125.4(2) yes
C102 . C106 . C137 . 118.0(2) yes
C111 . C106 . C137 . 116.6(2) yes
C108 . N107 . C111 . 109.5(2) yes
C108 . N107 . H1071 . 125.5(12) no
C111 . N107 . H1071 . 124.4(12) no
N107 . C108 . C109 . 107.2(2) yes
N107 . C108 . C112 . 126.3(2) yes
C109 . C108 . C112 . 126.5(2) yes
C108 . C109 . C110 . 108.0(2) yes
C108 . C109 . H1091 . 124.4 no
C110 . C109 . H1091 . 127.6 no
C109 . C110 . C111 . 108.2(2) yes
C109 . C110 . H1101 . 125.1 no
C111 . C110 . H1101 . 126.6 no
C110 . C111 . C106 . 125.8(2) yes
C110 . C111 . N107 . 107.1(2) yes
C106 . C111 . N107 . 127.1(2) yes
C105 2_665 C112 . C108 . 124.6(2) yes
C105 2_665 C112 . C147 . 117.8(2) yes
C108 . C112 . C147 . 117.5(2) yes
O132 . C133 . O131 . 124.0(3) yes
O132 . C133 . C134 . 118.0(3) yes
O131 . C133 . C134 . 118.0(3) yes
C133 . C134 . C135 . 120.8(2) yes
C133 . C134 . C139 . 120.1(2) yes
C135 . C134 . C139 . 119.1(2) yes
C134 . C135 . C136 . 120.0(2) yes
C134 . C135 . H1351 . 117.3 no
C136 . C135 . H1351 . 122.7 no
C135 . C136 . C137 . 121.0(2) yes
C135 . C136 . H1361 . 120.5 no
C137 . C136 . H1361 . 118.5 no
C106 . C137 . C136 . 122.0(2) yes
C106 . C137 . C138 . 119.4(2) yes
C136 . C137 . C138 . 118.6(2) yes
C137 . C138 . C139 . 120.2(2) yes
C137 . C138 . H1381 . 121.3 no
C139 . C138 . H1381 . 118.5 no
C134 . C139 . C138 . 121.0(2) yes
C134 . C139 . H1391 . 118.9 no
C138 . C139 . H1391 . 120.1 no
O142 . C143 . O141 . 128.3(3) yes
O142 . C143 . C144 . 117.6(3) yes
O141 . C143 . C144 . 114.0(3) yes
C143 . C144 . C145 . 124.8(3) yes
C143 . C144 . C149 . 118.1(3) yes
C145 . C144 . C149 . 117.0(3) yes
C144 . C145 . C146 . 123.2(3) yes
C144 . C145 . H1451 . 122.7 no
C146 . C145 . H1451 . 114.0 no
C145 . C146 . C147 . 118.7(3) yes
C145 . C146 . H1461 . 121.8 no
C147 . C146 . H1461 . 119.4 no
C112 . C147 . C146 . 123.0(3) yes
C112 . C147 . C148 . 119.5(2) yes
C146 . C147 . C148 . 117.6(3) yes
C147 . C148 . C149 . 123.2(3) yes
C147 . C148 . H1481 . 118.8 no
C149 . C148 . H1481 . 118.0 no
C148 . C149 . C144 . 120.2(3) yes
C148 . C149 . H1491 . 122.2 no
C144 . C149 . H1491 . 117.6 no
C203 . N201 . H2011 . 121.0(18) no
C203 . N201 . H2012 . 113.7(18) no
H2011 . N201 . H2012 . 111(4) no
C203 . N202 . H2021 . 121.6(17) no
C203 . N202 . H2022 . 118.9(17) no
H2021 . N202 . H2022 . 120(2) no
N201 . C203 . N202 . 121.3(4) yes
N201 . C203 . C207 . 119.5(4) yes
N202 . C203 . C207 . 119.2(3) yes
C206 . N204 . H2041 . 117.6(17) no
C206 . N204 . H2042 . 121.1(17) no
H2041 . N204 . H2042 . 120(3) no
C206 . N205 . H2051 . 120.6(18) no
C206 . N205 . H2052 . 119.2(17) no
H2051 . N205 . H2052 . 118(3) no
N205 . C206 . N204 . 121.3(4) yes
N205 . C206 . C210 . 120.1(3) yes
N204 . C206 . C210 . 118.6(3) yes
C203 . C207 . C208 . 119.5(3) yes
C203 . C207 . C212 . 121.5(3) yes
C208 . C207 . C212 . 119.0(3) yes
C207 . C208 . C209 . 119.9(3) yes
C207 . C208 . H2081 . 120.8 no
C209 . C208 . H2081 . 119.3 no
C208 . C209 . C210 . 121.0(3) yes
C208 . C209 . H2091 . 121.3 no
C210 . C209 . H2091 . 117.7 no
C206 . C210 . C209 . 119.5(3) yes
C206 . C210 . C211 . 120.9(3) yes
C209 . C210 . C211 . 119.6(3) yes
C210 . C211 . C212 . 119.7(3) yes
C210 . C211 . H2111 . 119.4 no
C212 . C211 . H2111 . 120.9 no
C207 . C212 . C211 . 120.9(3) yes
C207 . C212 . H2121 . 119.2 no
C211 . C212 . H2121 . 119.9 no
C223 . N221 . H2212 . 120.9(15) no
C223 . N221 . H2211 . 119.8(15) no
H2212 . N221 . H2211 . 119(2) no
C223 . N222 . H2221 . 118.8(16) no
C223 . N222 . H2222 . 119.1(16) no
H2221 . N222 . H2222 . 122(2) no
N222 . C223 . N221 . 121.8(2) yes
N222 . C223 . C227 . 118.4(2) yes
N221 . C223 . C227 . 119.8(2) yes
C226 . N224 . H2241 . 118.9(15) no
C226 . N224 . H2242 . 119.1(15) no
H2241 . N224 . H2242 . 121(2) no
C226 . N225 . H2251 . 118.3(15) no
C226 . N225 . H2252 . 120.7(16) no
H2251 . N225 . H2252 . 121(2) no
N224 . C226 . N225 . 121.9(2) yes
N224 . C226 . C230 . 118.3(2) yes
N225 . C226 . C230 . 119.8(2) yes
C223 . C227 . C228 . 119.6(2) yes
C223 . C227 . C232 . 119.5(2) yes
C228 . C227 . C232 . 120.9(2) yes
C227 . C228 . C229 . 119.5(3) yes
C227 . C228 . H2281 . 122.2 no
C229 . C228 . H2281 . 118.3 no
C228 . C229 . C230 . 119.4(3) yes
C228 . C229 . H2291 . 119.8 no
C230 . C229 . H2291 . 120.8 no
C226 . C230 . C229 . 119.8(2) yes
C226 . C230 . C231 . 119.6(2) yes
C229 . C230 . C231 . 120.7(2) yes
C230 . C231 . C232 . 119.9(2) yes
C230 . C231 . H2311 . 117.5 no
C232 . C231 . H2311 . 122.5 no
C227 . C232 . C231 . 119.5(2) yes
C227 . C232 . H2321 . 120.6 no
C231 . C232 . H2321 . 119.8 no
C243 . N241 . H2412 . 118.4(15) no
C243 . N241 . H2411 . 119.0(15) no
H2412 . N241 . H2411 . 122(2) no
C243 . N242 . H2422 . 120.3(15) no
C243 . N242 . H2421 . 120.6(15) no
H2422 . N242 . H2421 . 119(2) no
N241 . C243 . N242 . 121.6(2) yes
N241 . C243 . C244 . 118.3(2) yes
N242 . C243 . C244 . 120.1(2) yes
C243 . C244 . C245 . 120.3(2) yes
C243 . C244 . C246 . 119.5(2) yes
C245 . C244 . C246 . 120.2(2) yes
C244 . C245 . C246 2_556 119.8(2) yes
C244 . C245 . H2451 . 119.2 no
C246 2_556 C245 . H2451 . 121.0 no
C244 . C246 . C245 2_556 120.0(2) yes
C244 . C246 . H2461 . 121.2 no
C245 2_556 C246 . H2461 . 118.8 no
C263 . N261 . H2611 . 118.5(19) no
C263 . N261 . H2612 . 122.7(19) no
H2611 . N261 . H2612 . 119(3) no
C263 . N262 . H2621 . 121.1(19) no
C263 . N262 . H2622 . 121.1(19) no
H2621 . N262 . H2622 . 100(5) no
N262 . C263 . N261 . 123.9(5) yes
N262 . C263 . C264 . 117.5(5) yes
N261 . C263 . C264 . 118.6(4) yes
C263 . C264 . C265 . 117.7(4) yes
C263 . C264 . C266 . 118.7(4) yes
C265 . C264 . C266 . 123.6(4) yes
C264 . C265 . C266 2_575 118.1(4) yes
C264 . C265 . H2651 . 121.5 no
C266 2_575 C265 . H2651 . 120.4 no
C264 . C266 . C265 2_575 118.2(4) yes
C264 . C266 . H2661 . 119.2 no
C265 2_575 C266 . H2661 . 122.6 no
C2 . N1 . C5 . 105.5(2) yes
N1 . C2 . C3 . 111.0(2) yes
N1 . C2 . C24 . 125.3(2) yes
C3 . C2 . C24 . 123.7(2) yes
C2 . C3 . C4 . 105.9(2) yes
C2 . C3 . H31 . 126.7 no
C4 . C3 . H31 . 127.3 no
C3 . C4 . C5 . 107.3(2) yes
C3 . C4 . H41 . 127.0 no
C5 . C4 . H41 . 125.7 no
C4 . C5 . N1 . 110.2(2) yes
C4 . C5 . C6 . 123.9(2) yes
N1 . C5 . C6 . 125.8(2) yes
C5 . C6 . C8 . 124.9(2) yes
C5 . C6 . C67 . 118.8(2) yes
C8 . C6 . C67 . 116.2(2) yes
C8 . N7 . C11 . 110.3(2) yes
C8 . N7 . H71 . 125.5(12) no
C11 . N7 . H71 . 124.2(12) no
C6 . C8 . N7 . 125.9(2) yes
C6 . C8 . C9 . 127.6(2) yes
N7 . C8 . C9 . 106.3(2) yes
C8 . C9 . C10 . 108.5(2) yes
C8 . C9 . H91 . 125.6 no
C10 . C9 . H91 . 125.9 no
C9 . C10 . C11 . 108.0(2) yes
C9 . C10 . H101 . 128.3 no
C11 . C10 . H101 . 123.6 no
C10 . C11 . N7 . 106.7(2) yes
C10 . C11 . C12 . 126.6(2) yes
N7 . C11 . C12 . 126.7(2) yes
C11 . C12 . C14 . 124.6(2) yes
C11 . C12 . C57 . 115.9(2) yes
C14 . C12 . C57 . 119.4(2) yes
C14 . N13 . C17 . 105.5(2) yes
C12 . C14 . N13 . 125.8(2) yes
C12 . C14 . C15 . 123.3(2) yes
N13 . C14 . C15 . 110.9(2) yes
C14 . C15 . C16 . 106.4(2) yes
C14 . C15 . H151 . 125.6 no
C16 . C15 . H151 . 128.0 no
C15 . C16 . C17 . 106.4(2) yes
C15 . C16 . H161 . 128.3 no
C17 . C16 . H161 . 125.1 no
C16 . C17 . N13 . 110.8(2) yes
C16 . C17 . C18 . 123.3(2) yes
N13 . C17 . C18 . 126.0(2) yes
C17 . C18 . C20 . 124.4(2) yes
C17 . C18 . C47 . 118.1(2) yes
C20 . C18 . C47 . 117.5(2) yes
C20 . N19 . C23 . 110.5(2) yes
C20 . N19 . H191 . 124.8(12) no
C23 . N19 . H191 . 124.5(12) no
C18 . C20 . N19 . 126.1(2) yes
C18 . C20 . C21 . 127.4(2) yes
N19 . C20 . C21 . 106.5(2) yes
C20 . C21 . C22 . 108.5(2) yes
C20 . C21 . H211 . 125.4 no
C22 . C21 . H211 . 126.0 no
C21 . C22 . C23 . 107.9(2) yes
C21 . C22 . H221 . 128.6 no
C23 . C22 . H221 . 123.5 no
C22 . C23 . N19 . 106.6(2) yes
C22 . C23 . C24 . 126.8(2) yes
N19 . C23 . C24 . 126.5(2) yes
C2 . C24 . C23 . 125.7(2) yes
C2 . C24 . C37 . 118.2(2) yes
C23 . C24 . C37 . 116.1(2) yes
O31 . C33 . O32 . 125.2(3) yes
O31 . C33 . C34 . 117.0(3) yes
O32 . C33 . C34 . 117.8(3) yes
C33 . C34 . C35 . 121.1(3) yes
C33 . C34 . C39 . 120.1(3) yes
C35 . C34 . C39 . 118.8(2) yes
C34 . C35 . C36 . 120.7(3) yes
C34 . C35 . H351 . 118.5 no
C36 . C35 . H351 . 120.7 no
C35 . C36 . C37 . 120.5(3) yes
C35 . C36 . H361 . 118.4 no
C37 . C36 . H361 . 121.1 no
C24 . C37 . C36 . 121.7(2) yes
C24 . C37 . C38 . 120.1(2) yes
C36 . C37 . C38 . 118.2(2) yes
C37 . C38 . C39 . 120.9(2) yes
C37 . C38 . H381 . 117.0 no
C39 . C38 . H381 . 122.1 no
C38 . C39 . C34 . 120.8(3) yes
C38 . C39 . H391 . 118.9 no
C34 . C39 . H391 . 120.3 no
O42 . C43 . O41 . 124.5(2) yes
O42 . C43 . C44 . 117.7(2) yes
O41 . C43 . C44 . 117.8(2) yes
C43 . C44 . C45 . 120.3(2) yes
C43 . C44 . C49 . 120.3(2) yes
C45 . C44 . C49 . 119.4(2) yes
C44 . C45 . C46 . 120.1(2) yes
C44 . C45 . H451 . 121.4 no
C46 . C45 . H451 . 118.4 no
C45 . C46 . C47 . 120.9(2) yes
C45 . C46 . H461 . 119.4 no
C47 . C46 . H461 . 119.7 no
C18 . C47 . C46 . 121.2(2) yes
C18 . C47 . C48 . 120.2(2) yes
C46 . C47 . C48 . 118.6(2) yes
C47 . C48 . C49 . 120.6(2) yes
C47 . C48 . H481 . 119.7 no
C49 . C48 . H481 . 119.7 no
C44 . C49 . C48 . 120.4(2) yes
C44 . C49 . H491 . 118.2 no
C48 . C49 . H491 . 121.4 no
O52 . C53 . O51 . 122.0(4) yes
O52 . C53 . C54 . 120.3(4) yes
O51 . C53 . C54 . 117.7(4) yes
C53 . C54 . C55 . 122.6(4) yes
C53 . C54 . C59 . 117.5(4) yes
C55 . C54 . C59 . 119.9(3) yes
C54 . C55 . C56 . 120.4(3) yes
C54 . C55 . H551 . 120.6 no
C56 . C55 . H551 . 119.0 no
C55 . C56 . C57 . 119.6(3) yes
C55 . C56 . H561 . 120.7 no
C57 . C56 . H561 . 119.7 no
C12 . C57 . C56 . 120.5(2) yes
C12 . C57 . C58 . 120.0(3) yes
C56 . C57 . C58 . 119.4(3) yes
C57 . C58 . C59 . 120.8(3) yes
C57 . C58 . H581 . 118.6 no
C59 . C58 . H581 . 120.6 no
C54 . C59 . C58 . 119.8(3) yes
C54 . C59 . H591 . 119.7 no
C58 . C59 . H591 . 120.6 no
O62 . C63 . O61 . 123.4(2) yes
O62 . C63 . C64 . 118.1(2) yes
O61 . C63 . C64 . 118.5(2) yes
C63 . C64 . C65 . 119.8(2) yes
C63 . C64 . C69 . 120.9(2) yes
C65 . C64 . C69 . 119.3(2) yes
C64 . C65 . C66 . 120.2(2) yes
C64 . C65 . H651 . 121.5 no
C66 . C65 . H651 . 118.3 no
C65 . C66 . C67 . 120.9(2) yes
C65 . C66 . H661 . 120.7 no
C67 . C66 . H661 . 118.4 no
C6 . C67 . C66 . 121.0(2) yes
C6 . C67 . C68 . 120.6(2) yes
C66 . C67 . C68 . 118.4(2) yes
C67 . C68 . C69 . 121.0(2) yes
C67 . C68 . H681 . 119.0 no
C69 . C68 . H681 . 120.0 no
C64 . C69 . C68 . 120.2(2) yes
C64 . C69 . H691 . 120.3 no
C68 . C69 . H691 . 119.5 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C138 . H1381 . O61 . 152.65(8) 0.935 2.382 3.241(4) yes
C229 . H2291 . O132 . 156.23(8) 0.925 2.565 3.431(4) yes
C245 . H2451 . O42 2_665 148.12(8) 0.945 2.448 3.288(4) yes
C48 . H481 . O131 2_665 147.16(8) 0.960 2.508 3.355(4) yes
N225 . H2251 . O62 . 160(3) 0.871 2.047 2.879(4) yes
N7 . H71 . N1 . 120.5(15) 0.871 2.358 2.899(4) yes
N7 . H71 . N13 . 121.3(15) 0.871 2.358 2.908(4) yes
N225 . H2252 . O141 2_666 166(2) 0.858 2.109 2.950(4) yes
N222 . H2222 . O41 1_446 176(3) 0.867 1.912 2.777(4) yes
N242 . H2422 . O132 . 162(3) 0.872 2.000 2.843(4) yes
N19 . H191 . N1 . 120.2(15) 0.872 2.403 2.939(4) yes
N19 . H191 . N13 . 120.9(15) 0.872 2.360 2.906(4) yes
N224 . H2242 . O61 . 167(3) 0.873 1.962 2.818(4) yes
N242 . H2421 . O31 2_666 167(3) 0.872 1.880 2.737(4) yes
N241 . H2411 . O131 . 169(3) 0.869 1.952 2.810(4) yes
N221 . H2211 . O42 1_446 174(2) 0.868 1.921 2.786(4) yes
N107 . H1071 . N101 . 120.6(15) 0.851 2.413 2.939(4) yes
N107 . H1071 . N101 2_665 121.0(15) 0.851 2.364 2.896(4) yes
N204 . H2041 . O51 1_556 140(3) 0.869 2.353 3.073(4) yes
N204 . H2042 . O141 2_666 154(5) 0.868 2.253 3.057(4) yes
N205 . H2051 . O51 1_556 149(4) 0.862 2.010 2.786(4) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 22/02/17 at 15:54:49
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (  101 ,X'S,U'S)  UNTIL C    (   69 ) 
CONT H    ( 2251 ,X'S)  UNTIL H    ( 2052 ) 
RIDE C   ( 103,X'S) H   (1031,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) 
RIDE C   ( 109,X'S) H   (1091,X'S) 
RIDE C   ( 110,X'S) H   (1101,X'S) 
RIDE C   ( 135,X'S) H   (1351,X'S) 
RIDE C   ( 136,X'S) H   (1361,X'S) 
RIDE C   ( 138,X'S) H   (1381,X'S) 
RIDE C   ( 139,X'S) H   (1391,X'S) 
RIDE C   ( 145,X'S) H   (1451,X'S) 
RIDE C   ( 146,X'S) H   (1461,X'S) 
RIDE C   ( 148,X'S) H   (1481,X'S) 
RIDE C   ( 149,X'S) H   (1491,X'S) 
RIDE C   ( 208,X'S) H   (2081,X'S) 
RIDE C   ( 209,X'S) H   (2091,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) 
RIDE C   ( 228,X'S) H   (2281,X'S) 
RIDE C   ( 229,X'S) H   (2291,X'S) 
RIDE C   ( 231,X'S) H   (2311,X'S) 
RIDE C   ( 232,X'S) H   (2321,X'S) 
RIDE C   ( 245,X'S) H   (2451,X'S) 
RIDE C   ( 246,X'S) H   (2461,X'S) 
RIDE C   ( 265,X'S) H   (2651,X'S) 
RIDE C   ( 266,X'S) H   (2661,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
END      
;

_iucr_refine_instructions_details_restraints 
;                                                                       
#
# Punched on 22/02/17 at 15:54:49
#
#LIST     16                                                                    
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 107) TO H(1071) 
REST 0.028, 0.002 = H(1071,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(1071) TO N ( 107) TO C(108) 
CONT H(1071) TO N ( 107) TO C(111) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 201) TO H(2011) 
CONT N ( 201) TO H(2012) 
REST 0.081, 0.002 = H(2011,U[ISO]) 
REST 0.081, 0.002 = H(2012,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(203) TO N ( 201) TO H(2011) 
CONT C(203) TO N ( 201) TO H(2012) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 202) TO H(2021) 
CONT N ( 202) TO H(2022) 
REST 0.071, 0.002 = H(2021,U[ISO]) 
REST 0.071, 0.002 = H(2022,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(203) TO N ( 202) TO H(2021) 
CONT C(203) TO N ( 202) TO H(2022) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 204) TO H(2041) 
CONT N ( 204) TO H(2042) 
REST 0.068, 0.002 = H(2041,U[ISO]) 
REST 0.068, 0.002 = H(2042,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(206) TO N ( 204) TO H(2041) 
CONT C(206) TO N ( 204) TO H(2042) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 205) TO H(2051) 
CONT N ( 205) TO H(2052) 
REST 0.072, 0.002 = H(2051,U[ISO]) 
REST 0.072, 0.002 = H(2052,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(206) TO N ( 205) TO H(2051) 
CONT C(206) TO N ( 205) TO H(2052) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 221) TO H(2212) 
CONT N ( 221) TO H(2211) 
REST 0.032, 0.002 = H(2212,U[ISO]) 
REST 0.032, 0.002 = H(2211,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(223) TO N ( 221) TO H(2212) 
CONT C(223) TO N ( 221) TO H(2211) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 222) TO H(2221) 
CONT N ( 222) TO H(2222) 
REST 0.038, 0.002 = H(2221,U[ISO]) 
REST 0.038, 0.002 = H(2222,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(223) TO N ( 222) TO H(2221) 
CONT C(223) TO N ( 222) TO H(2222) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 224) TO H(2241) 
CONT N ( 224) TO H(2242) 
REST 0.031, 0.002 = H(2241,U[ISO]) 
REST 0.031, 0.002 = H(2242,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(226) TO N ( 224) TO H(2241) 
CONT C(226) TO N ( 224) TO H(2242) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 225) TO H(2251) 
CONT N ( 225) TO H(2252) 
REST 0.033, 0.002 = H(2251,U[ISO]) 
REST 0.033, 0.002 = H(2252,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(226) TO N ( 225) TO H(2251) 
CONT C(226) TO N ( 225) TO H(2252) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 241) TO H(2412) 
CONT N ( 241) TO H(2411) 
REST 0.031, 0.002 = H(2412,U[ISO]) 
REST 0.031, 0.002 = H(2411,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(243) TO N ( 241) TO H(2412) 
CONT C(243) TO N ( 241) TO H(2411) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 242) TO H(2422) 
CONT N ( 242) TO H(2421) 
REST 0.034, 0.002 = H(2422,U[ISO]) 
REST 0.034, 0.002 = H(2421,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(243) TO N ( 242) TO H(2422) 
CONT C(243) TO N ( 242) TO H(2421) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 261) TO H(2611) 
CONT N ( 261) TO H(2612) 
REST 0.122, 0.002 = H(2611,U[ISO]) 
REST 0.122, 0.002 = H(2612,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(263) TO N ( 261) TO H(2611) 
CONT C(263) TO N ( 261) TO H(2612) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 262) TO H(2621) 
CONT N ( 262) TO H(2622) 
REST 0.138, 0.002 = H(2621,U[ISO]) 
REST 0.138, 0.002 = H(2622,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(263) TO N ( 262) TO H(2621) 
CONT C(263) TO N ( 262) TO H(2622) 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 7) TO H(71) 
REST 0.025, 0.002 = H(71,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(71) TO N ( 7) TO C(8) 
CONT H(71) TO N ( 7) TO C(11) 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 19) TO H(191) 
REST 0.026, 0.002 = H(191,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(191) TO N ( 19) TO C(20) 
CONT H(191) TO N ( 19) TO C(23) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM 
REM POORLY-BEHAVED BENZOATES 
REM 
DIST 1.40, 0.005= C(54) TO C(55), C(55) TO C(56) 
CONT C(56) TO C(57), C(57) TO C(58) 
CONT C(58) TO C(59), C(59) TO C(54) 
CONT C(144) TO C(145), C(145) TO C(146) 
CONT C(146) TO C(147), C(147) TO C(148) 
CONT C(148) TO C(149), C(149) TO C(144) 
DIST 1.49, 0.005 = C(53) TO C(54), C(143) TO C(144) 
DIST 1.25, 0.005 = O(51) TO C(53), O(52) TO C(53) 
CONT O(141) TO C(143), O(142) TO C(143) 
REM POORLY-BEHAVED AMIDINIUM 
DIST 1.31, 0.005 = N(261) TO C(263), N(262) TO C(263) 
DIST 1.49, 0.005 = C(263) TO C(264) 
DIST 1.40, 0.005 = C(264) TO C(265), C(264) TO C(266) 
CONT C(265) TO C(266,-1,1,0,2), C(266) TO C(265,-1,1,0,2) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00100 = O(141) TO C(143) 
VIBR .0, 0.00100 = O(142) TO C(143) 
VIBR .0, 0.00100 = C(143) TO C(144) 
VIBR .0, 0.00200 = O(141) TO O(142) 
VIBR .0, 0.00200 = C(144) TO O(142) 
VIBR .0, 0.00200 = C(144) TO O(141) 
VIBR .0, 0.00100 = C(144) TO C(145) 
VIBR .0, 0.00100 = C(144) TO C(149) 
VIBR .0, 0.00200 = C(145) TO C(143) 
VIBR .0, 0.00200 = C(149) TO C(143) 
VIBR .0, 0.00200 = C(149) TO C(145) 
VIBR .0, 0.00100 = C(145) TO C(146) 
VIBR .0, 0.00200 = C(146) TO C(144) 
VIBR .0, 0.00100 = C(146) TO C(147) 
VIBR .0, 0.00200 = C(147) TO C(145) 
VIBR .0, 0.00100 = C(147) TO C(148) 
VIBR .0, 0.00200 = C(146) TO C(112) 
VIBR .0, 0.00200 = C(148) TO C(112) 
VIBR .0, 0.00200 = C(148) TO C(146) 
VIBR .0, 0.00100 = C(148) TO C(149) 
VIBR .0, 0.00200 = C(149) TO C(147) 
VIBR .0, 0.00200 = C(148) TO C(144) 
VIBR .0, 0.00100 = N(261) TO C(263) 
VIBR .0, 0.00100 = N(262) TO C(263) 
VIBR .0, 0.00100 = C(263) TO C(264) 
VIBR .0, 0.00200 = N(261) TO N(262) 
VIBR .0, 0.00200 = C(264) TO N(262) 
VIBR .0, 0.00200 = C(264) TO N(261) 
VIBR .0, 0.00100 = C(264) TO C(265) 
VIBR .0, 0.00100 = C(264) TO C(266) 
VIBR .0, 0.00200 = C(265) TO C(263) 
VIBR .0, 0.00200 = C(266) TO C(263) 
VIBR .0, 0.00200 = C(266) TO C(265) 
VIBR .0, 0.00100 = C(265) TO C(266,-1,1,0,2) 
VIBR .0, 0.00200 = C(266,-1,1,0,2) TO C(264) 
VIBR .0, 0.00200 = C(264) TO C(265,-1,1,0,2) 
VIBR .0, 0.00100 = C(48) TO C(49) 
VIBR .0, 0.00200 = C(49) TO C(47) 
VIBR .0, 0.00200 = C(44) TO C(48) 
VIBR .0, 0.00100 = O(51) TO C(53) 
VIBR .0, 0.00100 = O(52) TO C(53) 
VIBR .0, 0.00100 = C(53) TO C(54) 
VIBR .0, 0.00200 = O(51) TO O(52) 
VIBR .0, 0.00200 = C(54) TO O(52) 
VIBR .0, 0.00200 = C(54) TO O(51) 
VIBR .0, 0.00100 = C(54) TO C(55) 
VIBR .0, 0.00100 = C(54) TO C(59) 
VIBR .0, 0.00200 = C(55) TO C(53) 
VIBR .0, 0.00200 = C(59) TO C(53) 
VIBR .0, 0.00200 = C(59) TO C(55) 
VIBR .0, 0.00100 = C(55) TO C(56) 
VIBR .0, 0.00200 = C(56) TO C(54) 
VIBR .0, 0.00100 = C(56) TO C(57) 
VIBR .0, 0.00200 = C(57) TO C(55) 
VIBR .0, 0.00100 = C(57) TO C(58) 
VIBR .0, 0.00200 = C(56) TO C(12) 
VIBR .0, 0.00200 = C(58) TO C(12) 
VIBR .0, 0.00200 = C(58) TO C(56) 
VIBR .0, 0.00100 = C(58) TO C(59) 
VIBR .0, 0.00200 = C(59) TO C(57) 
VIBR .0, 0.00200 = C(54) TO C(58) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.02000 = O(141) TO C(143) 
U(IJ) .0, 0.02000 = O(142) TO C(143) 
U(IJ) .0, 0.01000 = C(143) TO C(144) 
U(IJ) .0, 0.01000 = C(144) TO C(145) 
U(IJ) .0, 0.01000 = C(144) TO C(149) 
U(IJ) .0, 0.01000 = C(145) TO C(146) 
U(IJ) .0, 0.01000 = C(146) TO C(147) 
U(IJ) .0, 0.01000 = C(147) TO C(148) 
U(IJ) .0, 0.01000 = C(148) TO C(149) 
U(IJ) .0, 0.02000 = N(261) TO C(263) 
U(IJ) .0, 0.02000 = N(262) TO C(263) 
U(IJ) .0, 0.01000 = C(263) TO C(264) 
U(IJ) .0, 0.01000 = C(264) TO C(265) 
U(IJ) .0, 0.01000 = C(264) TO C(266) 
U(IJ) .0, 0.01000 = C(265) TO C(266,-1,1,0,2) 
U(IJ) .0, 0.02000 = O(51) TO C(53) 
U(IJ) .0, 0.02000 = O(52) TO C(53) 
U(IJ) .0, 0.01000 = C(53) TO C(54) 
U(IJ) .0, 0.01000 = C(54) TO C(55) 
U(IJ) .0, 0.01000 = C(54) TO C(59) 
U(IJ) .0, 0.01000 = C(55) TO C(56) 
U(IJ) .0, 0.01000 = C(56) TO C(57) 
U(IJ) .0, 0.01000 = C(57) TO C(58) 
U(IJ) .0, 0.01000 = C(58) TO C(59) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-2 3 1 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5_pyridine
_database_code_depnum_ccdc_archive 'CCDC 1574952'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT097_COMPOUNDNAME        
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.83 eA-3  
RESPONSE: This small peak is located close to the diethyl ether solvent 
molecule, and may result from minor positional disorder of this group - however
it was not possible to model this.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
The asymmetric unit cell contains half of the compound as well as two pyridine
and one diethyl ether solvates.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement.
;

_cell_length_a                   14.7549(5)
_cell_length_b                   7.3113(3)
_cell_length_c                   30.7507(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.163(4)
_cell_angle_gamma                90
_cell_volume                     3314.95(13)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C38 H35 N4 O5'
_chemical_formula_moiety         '0.5(C48 H30 N4 O8), 2(C5 H5 N), C4 H10 O '
_chemical_compound_source        synthesized
_chemical_formula_weight         627.72

_cell_measurement_reflns_used    2074
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      66.2
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_max          0.11

_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1324
_exptl_absorpt_coefficient_mu    0.682

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            17673
_reflns_number_total             5994
_diffrn_reflns_av_R_equivalents  0.060

_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         68.235
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        68.235
_diffrn_measured_fraction_theta_full 0.988

_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_reflns_limit_h_min              -17
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              36

_oxford_diffrn_Wilson_B_factor   2.52
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.49
_refine_diff_density_max         0.83

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5079
_refine_ls_number_restraints     5
_refine_ls_number_parameters     433
_oxford_refine_ls_R_factor_ref   0.0971
_refine_ls_wR_factor_ref         0.1424
_refine_ls_goodness_of_fit_ref   0.9936
_refine_ls_shift/su_max          0.0002954
_refine_ls_shift/su_mean         0.0000335

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5080
_refine_ls_R_factor_all          0.0971
_refine_ls_wR_factor_all         0.1425

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3431
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_gt          0.1233

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.93P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N101 N -0.1868(2) 1.4386(4) 0.40873(11) 0.0489 1.0000 Uani . . . . . .
C102 C -0.2341(3) 1.3904(5) 0.37278(14) 0.0540 1.0000 Uani . . . . . .
C103 C -0.3225(3) 1.4433(5) 0.36379(14) 0.0523 1.0000 Uani . . . . . .
C104 C -0.3641(2) 1.5471(5) 0.39465(14) 0.0489 1.0000 Uani . . . . . .
C105 C -0.3165(3) 1.5972(5) 0.43154(13) 0.0456 1.0000 Uani . . . . . .
C106 C -0.2289(3) 1.5404(5) 0.43719(13) 0.0481 1.0000 Uani . . . . . .
N111 N 0.7018(2) 1.6450(4) 0.77889(9) 0.0447 1.0000 Uani . . . . . .
C112 C 0.7667(3) 1.7583(5) 0.76622(13) 0.0550 1.0000 Uani . . . . . .
C113 C 0.8417(3) 1.8004(6) 0.79146(14) 0.0622 1.0000 Uani . . . . . .
C114 C 0.8511(3) 1.7229(6) 0.83234(14) 0.0596 1.0000 Uani . . . . . .
C115 C 0.7844(3) 1.6089(5) 0.84627(12) 0.0501 1.0000 Uani . . . . . .
C116 C 0.7116(3) 1.5723(5) 0.81850(12) 0.0474 1.0000 Uani . . . . . .
N1 N 0.39795(16) 0.4675(3) 0.45411(8) 0.0247 1.0000 Uani . . . . . .
C2 C 0.39403(19) 0.3385(4) 0.42179(10) 0.0254 1.0000 Uani . . . . . .
C3 C 0.3110(2) 0.3582(4) 0.39501(10) 0.0283 1.0000 Uani . . . . . .
C4 C 0.2658(2) 0.5010(4) 0.41113(10) 0.0278 1.0000 Uani . . . . . .
C5 C 0.3198(2) 0.5685(4) 0.44831(10) 0.0258 1.0000 Uani . . . . . .
C6 C 0.2959(2) 0.7184(4) 0.47392(10) 0.0245 1.0000 Uani . . . . . .
C7 C 0.3480(2) 0.7877(4) 0.50881(10) 0.0256 1.0000 Uani D . . . . .
C8 C 0.3211(2) 0.9244(4) 0.53922(10) 0.0290 1.0000 Uani . . . . . .
C9 C 0.3889(2) 0.9470(4) 0.56948(10) 0.0283 1.0000 Uani . . . . . .
C10 C 0.4613(2) 0.8237(4) 0.55986(10) 0.0261 1.0000 Uani D . . . . .
N11 N 0.43371(16) 0.7319(3) 0.52258(8) 0.0265 1.0000 Uani D . . . . .
C12 C 0.5406(2) 0.7962(4) 0.58517(10) 0.0264 1.0000 Uani . . . . . .
C13 C 0.2088(2) 0.8150(4) 0.46367(9) 0.0254 1.0000 Uani . . . . . .
C14 C 0.1254(2) 0.7254(4) 0.46379(10) 0.0290 1.0000 Uani . . . . . .
C15 C 0.0456(2) 0.8198(4) 0.45475(10) 0.0313 1.0000 Uani . . . . . .
C16 C 0.0471(2) 1.0057(4) 0.44623(10) 0.0297 1.0000 Uani . . . . . .
C17 C 0.1293(2) 1.0964(4) 0.44580(10) 0.0332 1.0000 Uani . . . . . .
C18 C 0.2095(2) 1.0019(4) 0.45440(10) 0.0316 1.0000 Uani . . . . . .
C19 C -0.0403(2) 1.1037(5) 0.43617(10) 0.0360 1.0000 Uani . . . . . .
O20 O -0.11287(15) 1.0244(4) 0.43501(8) 0.0438 1.0000 Uani . . . . . .
O21 O -0.03008(17) 1.2807(4) 0.42920(10) 0.0536 1.0000 Uani D . . . . .
C22 C 0.55463(19) 0.9229(4) 0.62291(10) 0.0253 1.0000 Uani . . . . . .
C23 C 0.5677(2) 1.1097(4) 0.61569(10) 0.0272 1.0000 Uani . . . . . .
C24 C 0.5814(2) 1.2296(4) 0.65029(10) 0.0289 1.0000 Uani . . . . . .
C25 C 0.5826(2) 1.1647(4) 0.69253(10) 0.0271 1.0000 Uani . . . . . .
C26 C 0.5690(2) 0.9787(4) 0.70014(10) 0.0309 1.0000 Uani . . . . . .
C27 C 0.5551(2) 0.8596(4) 0.66574(10) 0.0301 1.0000 Uani . . . . . .
C28 C 0.6031(2) 1.2881(4) 0.73032(11) 0.0332 1.0000 Uani . . . . . .
O29 O 0.60538(18) 1.4630(3) 0.71922(8) 0.0412 1.0000 Uani D . . . . .
O30 O 0.61678(19) 1.2331(3) 0.76707(7) 0.0446 1.0000 Uani . . . . . .
C121 C 0.8336(4) 1.2835(10) 0.7051(2) 0.1108 1.0000 Uani . . . . . .
C122 C 0.8473(4) 1.1277(9) 0.6754(2) 0.1048 1.0000 Uani . . . . . .
O123 O 0.9100(3) 1.0079(6) 0.69768(12) 0.0911 1.0000 Uani . . . . . .
C124 C 0.9333(5) 0.8661(10) 0.67183(17) 0.1086 1.0000 Uani . . . . . .
C125 C 1.0007(4) 0.7408(9) 0.6924(2) 0.1106 1.0000 Uani . . . . . .
H1021 H -0.2043 1.3212 0.3522 0.0643 1.0000 Uiso R . . . . .
H1031 H -0.3526 1.4094 0.3378 0.0627 1.0000 Uiso R . . . . .
H1041 H -0.4247 1.5834 0.3902 0.0593 1.0000 Uiso R . . . . .
H1051 H -0.3430 1.6688 0.4532 0.0552 1.0000 Uiso R . . . . .
H1061 H -0.1965 1.5743 0.4629 0.0603 1.0000 Uiso R . . . . .
H1121 H 0.7609 1.8112 0.7383 0.0652 1.0000 Uiso R . . . . .
H1131 H 0.8856 1.8802 0.7807 0.0750 1.0000 Uiso R . . . . .
H1141 H 0.9025 1.7480 0.8503 0.0711 1.0000 Uiso R . . . . .
H1151 H 0.7882 1.5572 0.8743 0.0628 1.0000 Uiso R . . . . .
H1161 H 0.6661 1.4924 0.8276 0.0562 1.0000 Uiso R . . . . .
H31 H 0.2931 0.2875 0.3711 0.0348 1.0000 Uiso R . . . . .
H41 H 0.2105 0.5478 0.4003 0.0342 1.0000 Uiso R . . . . .
H81 H 0.2657 0.9856 0.5380 0.0344 1.0000 Uiso R . . . . .
H91 H 0.3886 1.0278 0.5934 0.0357 1.0000 Uiso R . . . . .
H141 H 0.1240 0.5994 0.4697 0.0340 1.0000 Uiso R . . . . .
H151 H -0.0084 0.7579 0.4551 0.0369 1.0000 Uiso R . . . . .
H171 H 0.1306 1.2221 0.4392 0.0403 1.0000 Uiso R . . . . .
H181 H 0.2642 1.0659 0.4540 0.0376 1.0000 Uiso R . . . . .
H231 H 0.5669 1.1521 0.5866 0.0329 1.0000 Uiso R . . . . .
H241 H 0.5906 1.3534 0.6450 0.0350 1.0000 Uiso R . . . . .
H261 H 0.5690 0.9362 0.7289 0.0386 1.0000 Uiso R . . . . .
H271 H 0.5453 0.7347 0.6712 0.0376 1.0000 Uiso R . . . . .
H1211 H 0.7881 1.3663 0.6923 0.1632 1.0000 Uiso R . . . . .
H1212 H 0.8908 1.3489 0.7102 0.1632 1.0000 Uiso R . . . . .
H1213 H 0.8143 1.2384 0.7333 0.1629 1.0000 Uiso R . . . . .
H1221 H 0.8755 1.1722 0.6487 0.1221 1.0000 Uiso R . . . . .
H1222 H 0.7892 1.0652 0.6679 0.1222 1.0000 Uiso R . . . . .
H1241 H 0.9579 0.9164 0.6448 0.1372 1.0000 Uiso R . . . . .
H1242 H 0.8774 0.7980 0.6649 0.1375 1.0000 Uiso R . . . . .
H1253 H 1.0159 0.6440 0.6723 0.1680 1.0000 Uiso R . . . . .
H1252 H 1.0560 0.8072 0.7011 0.1685 1.0000 Uiso R . . . . .
H1251 H 0.9767 0.6867 0.7189 0.1682 1.0000 Uiso R . . . . .
H111 H 0.4643(14) 0.649(4) 0.5100(8) 0.0322 1.0000 Uiso D . . . . .
H291 H 0.629(3) 1.521(5) 0.7399(10) 0.0625 1.0000 Uiso D . . . . .
H211 H -0.0821(18) 1.327(6) 0.4226(15) 0.0801 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.14(7)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N101 . C102 . 1.332(5) yes
N101 . C106 . 1.322(5) yes
C102 . C103 . 1.379(6) yes
C102 . H1021 . 0.933 no
C103 . C104 . 1.378(6) yes
C103 . H1031 . 0.933 no
C104 . C105 . 1.362(5) yes
C104 . H1041 . 0.937 no
C105 . C106 . 1.362(5) yes
C105 . H1051 . 0.942 no
C106 . H1061 . 0.943 no
N111 . C112 . 1.335(5) yes
N111 . C116 . 1.332(5) yes
C112 . C113 . 1.363(6) yes
C112 . H1121 . 0.942 no
C113 . C114 . 1.381(6) yes
C113 . H1131 . 0.941 no
C114 . C115 . 1.371(6) yes
C114 . H1141 . 0.941 no
C115 . C116 . 1.373(5) yes
C115 . H1151 . 0.940 no
C116 . H1161 . 0.939 no
N1 . C2 . 1.370(4) yes
N1 . C5 . 1.376(4) yes
C2 . C12 2_666 1.400(4) yes
C2 . C3 . 1.457(4) yes
C3 . C4 . 1.344(4) yes
C3 . H31 . 0.929 no
C4 . C5 . 1.454(4) yes
C4 . H41 . 0.935 no
C5 . C6 . 1.402(4) yes
C6 . C7 . 1.391(4) yes
C6 . C13 . 1.491(4) yes
C7 . C8 . 1.435(4) yes
C7 . N11 . 1.380(4) yes
C8 . C9 . 1.351(4) yes
C8 . H81 . 0.931 no
C9 . C10 . 1.437(4) yes
C9 . H91 . 0.944 no
C10 . N11 . 1.377(4) yes
C10 . C12 . 1.396(4) yes
N11 . H111 . 0.857(17) no
C12 . C22 . 1.493(4) yes
C13 . C14 . 1.394(4) yes
C13 . C18 . 1.396(4) yes
C14 . C15 . 1.383(4) yes
C14 . H141 . 0.940 no
C15 . C16 . 1.384(4) yes
C15 . H151 . 0.917 no
C16 . C17 . 1.382(5) yes
C16 . C19 . 1.498(4) yes
C17 . C18 . 1.388(4) yes
C17 . H171 . 0.941 no
C18 . H181 . 0.934 no
C19 . O20 . 1.217(4) yes
C19 . O21 . 1.321(4) yes
O21 . H211 . 0.855(18) no
C22 . C23 . 1.398(4) yes
C22 . C27 . 1.396(4) yes
C23 . C24 . 1.388(4) yes
C23 . H231 . 0.946 no
C24 . C25 . 1.383(4) yes
C24 . H241 . 0.931 no
C25 . C26 . 1.396(4) yes
C25 . C28 . 1.493(4) yes
C26 . C27 . 1.379(4) yes
C26 . H261 . 0.937 no
C27 . H271 . 0.941 no
C28 . O29 . 1.324(4) yes
C28 . O30 . 1.209(4) yes
O29 . H291 . 0.833(18) no
C121 . C122 . 1.478(8) yes
C121 . H1211 . 0.976 no
C121 . H1212 . 0.977 no
C121 . H1213 . 0.981 no
C122 . O123 . 1.429(6) yes
C122 . H1221 . 0.990 no
C122 . H1222 . 0.991 no
O123 . C124 . 1.359(6) yes
C124 . C125 . 1.476(7) yes
C124 . H1241 . 0.989 no
C124 . H1242 . 0.981 no
C125 . H1253 . 0.972 no
C125 . H1252 . 0.978 no
C125 . H1251 . 0.983 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C102 . N101 . C106 . 117.0(3) yes
N101 . C102 . C103 . 123.6(4) yes
N101 . C102 . H1021 . 117.5 no
C103 . C102 . H1021 . 118.8 no
C102 . C103 . C104 . 117.4(4) yes
C102 . C103 . H1031 . 120.9 no
C104 . C103 . H1031 . 121.7 no
C103 . C104 . C105 . 119.5(4) yes
C103 . C104 . H1041 . 120.2 no
C105 . C104 . H1041 . 120.3 no
C104 . C105 . C106 . 118.8(4) yes
C104 . C105 . H1051 . 121.5 no
C106 . C105 . H1051 . 119.7 no
C105 . C106 . N101 . 123.7(4) yes
C105 . C106 . H1061 . 118.4 no
N101 . C106 . H1061 . 117.9 no
C112 . N111 . C116 . 117.4(3) yes
N111 . C112 . C113 . 123.3(4) yes
N111 . C112 . H1121 . 118.6 no
C113 . C112 . H1121 . 118.0 no
C112 . C113 . C114 . 118.5(4) yes
C112 . C113 . H1131 . 119.7 no
C114 . C113 . H1131 . 121.8 no
C113 . C114 . C115 . 119.1(4) yes
C113 . C114 . H1141 . 120.4 no
C115 . C114 . H1141 . 120.5 no
C114 . C115 . C116 . 118.6(4) yes
C114 . C115 . H1151 . 120.8 no
C116 . C115 . H1151 . 120.6 no
C115 . C116 . N111 . 123.1(4) yes
C115 . C116 . H1161 . 119.1 no
N111 . C116 . H1161 . 117.8 no
C2 . N1 . C5 . 105.3(2) yes
C12 2_666 C2 . N1 . 125.8(3) yes
C12 2_666 C2 . C3 . 123.5(3) yes
N1 . C2 . C3 . 110.7(3) yes
C2 . C3 . C4 . 106.7(3) yes
C2 . C3 . H31 . 126.9 no
C4 . C3 . H31 . 126.4 no
C3 . C4 . C5 . 106.8(3) yes
C3 . C4 . H41 . 126.3 no
C5 . C4 . H41 . 127.0 no
C4 . C5 . N1 . 110.6(3) yes
C4 . C5 . C6 . 124.4(3) yes
N1 . C5 . C6 . 125.0(3) yes
C5 . C6 . C7 . 125.1(3) yes
C5 . C6 . C13 . 119.0(3) yes
C7 . C6 . C13 . 115.9(3) yes
C6 . C7 . C8 . 126.7(3) yes
C6 . C7 . N11 . 127.0(3) yes
C8 . C7 . N11 . 106.2(3) yes
C7 . C8 . C9 . 108.5(3) yes
C7 . C8 . H81 . 125.0 no
C9 . C8 . H81 . 126.5 no
C8 . C9 . C10 . 108.6(3) yes
C8 . C9 . H91 . 126.1 no
C10 . C9 . H91 . 125.3 no
C9 . C10 . N11 . 106.2(3) yes
C9 . C10 . C12 . 126.1(3) yes
N11 . C10 . C12 . 127.5(3) yes
C7 . N11 . C10 . 110.5(2) yes
C7 . N11 . H111 . 124.3(12) no
C10 . N11 . H111 . 125.2(12) no
C2 2_666 C12 . C10 . 125.7(3) yes
C2 2_666 C12 . C22 . 118.6(3) yes
C10 . C12 . C22 . 115.6(3) yes
C6 . C13 . C14 . 122.1(3) yes
C6 . C13 . C18 . 119.6(3) yes
C14 . C13 . C18 . 118.3(3) yes
C13 . C14 . C15 . 120.6(3) yes
C13 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 120.2 no
C14 . C15 . C16 . 120.6(3) yes
C14 . C15 . H151 . 119.0 no
C16 . C15 . H151 . 120.4 no
C15 . C16 . C17 . 119.5(3) yes
C15 . C16 . C19 . 119.3(3) yes
C17 . C16 . C19 . 121.1(3) yes
C16 . C17 . C18 . 120.1(3) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 120.2 no
C13 . C18 . C17 . 120.9(3) yes
C13 . C18 . H181 . 120.5 no
C17 . C18 . H181 . 118.6 no
C16 . C19 . O20 . 121.9(3) yes
C16 . C19 . O21 . 113.5(3) yes
O20 . C19 . O21 . 124.6(3) yes
C19 . O21 . H211 . 108(3) no
C12 . C22 . C23 . 119.9(3) yes
C12 . C22 . C27 . 121.5(3) yes
C23 . C22 . C27 . 118.6(3) yes
C22 . C23 . C24 . 120.8(3) yes
C22 . C23 . H231 . 118.3 no
C24 . C23 . H231 . 120.9 no
C23 . C24 . C25 . 120.0(3) yes
C23 . C24 . H241 . 119.9 no
C25 . C24 . H241 . 120.1 no
C24 . C25 . C26 . 119.7(3) yes
C24 . C25 . C28 . 121.3(3) yes
C26 . C25 . C28 . 119.0(3) yes
C25 . C26 . C27 . 120.3(3) yes
C25 . C26 . H261 . 119.1 no
C27 . C26 . H261 . 120.6 no
C22 . C27 . C26 . 120.6(3) yes
C22 . C27 . H271 . 119.7 no
C26 . C27 . H271 . 119.7 no
C25 . C28 . O29 . 112.9(3) yes
C25 . C28 . O30 . 123.3(3) yes
O29 . C28 . O30 . 123.8(3) yes
C28 . O29 . H291 . 108(3) no
C122 . C121 . H1211 . 109.8 no
C122 . C121 . H1212 . 109.8 no
H1211 . C121 . H1212 . 109.7 no
C122 . C121 . H1213 . 109.7 no
H1211 . C121 . H1213 . 110.3 no
H1212 . C121 . H1213 . 107.5 no
C121 . C122 . O123 . 106.2(5) yes
C121 . C122 . H1221 . 109.3 no
O123 . C122 . H1221 . 108.4 no
C121 . C122 . H1222 . 111.2 no
O123 . C122 . H1222 . 111.6 no
H1221 . C122 . H1222 . 110.1 no
C122 . O123 . C124 . 111.2(5) yes
O123 . C124 . C125 . 113.9(5) yes
O123 . C124 . H1241 . 108.5 no
C125 . C124 . H1241 . 109.1 no
O123 . C124 . H1242 . 106.5 no
C125 . C124 . H1242 . 109.0 no
H1241 . C124 . H1242 . 109.7 no
C124 . C125 . H1253 . 110.4 no
C124 . C125 . H1252 . 110.5 no
H1253 . C125 . H1252 . 109.1 no
C124 . C125 . H1251 . 110.3 no
H1253 . C125 . H1251 . 109.4 no
H1252 . C125 . H1251 . 107.1 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C103 . H1031 . O30 3_474 160.65(12) 0.933 2.439 3.333(5) yes
C115 . H1151 . O20 3_675 145.62(12) 0.940 2.402 3.222(5) yes
C8 . H81 . O20 2_576 142.70(9) 0.931 2.432 3.223(5) yes
N11 . H111 . N1 . 121.1(15) 0.857 2.355 2.892(5) yes
O29 . H291 . N111 . 169(4) 0.833 1.817 2.639(5) yes
O21 . H211 . N101 . 176(5) 0.855 1.785 2.639(5) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 04/02/17 at 16:26:10
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (  101 ,X'S,U'S)  UNTIL C    (  125 ) 
CONT H    (  111 ,X'S)  UNTIL H    (  211 ) 
RIDE C   ( 102,X'S) H   (1021,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) 
RIDE C   ( 105,X'S) H   (1051,X'S) 
RIDE C   ( 106,X'S) H   (1061,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) 
RIDE C   ( 115,X'S) H   (1151,X'S) 
RIDE C   ( 116,X'S) H   (1161,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   ( 121,X'S) H   (1211,X'S) H   (1212,X'S) H   (1213,X'S) 
RIDE C   ( 122,X'S) H   (1221,X'S) H   (1222,X'S) 
RIDE C   ( 124,X'S) H   (1241,X'S) H   (1242,X'S) 
RIDE C   ( 125,X'S) H   (1253,X'S) H   (1252,X'S) H   (1251,X'S) 
END  
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 04/02/17 at 16:26:10
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 11) TO H(111) 
REST 0.032, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO N ( 11) TO C(7) 
CONT H(111) TO N ( 11) TO C(10) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 21) TO H(211) 
REST 0.079, 0.002 = H(211,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 29) TO H(291) 
REST 0.062, 0.002 = H(291,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4_bpy_DMSO_acetone
_database_code_depnum_ccdc_archive 'CCDC 1574949'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
The asymmetric unit cell contains half of the compound as well as one
DMSO and one acetone solvate.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement.
;

_cell_length_a                   11.47610(10)
_cell_length_b                   28.7617(2)
_cell_length_c                   11.75310(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.3098(10)
_cell_angle_gamma                90
_cell_volume                     3506.99(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ni -3.0029 0.5091 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

_chemical_formula_sum            'C39 H34 N4 Ni0.5 O6 S1'
_chemical_formula_moiety         'C34 H22 N4 Ni0.5 O4, C2 H6 O S, C3 H6 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         716.15

_cell_measurement_reflns_used    35174
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      73.7
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_max          0.70

_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1496
_exptl_absorpt_coefficient_mu    1.528

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            56693
_reflns_number_total             7096
_diffrn_reflns_av_R_equivalents  0.031

_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         73.833
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        73.833
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -14
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              35
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   1.83
_oxford_diffrn_Wilson_scale      0.07

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.65
_refine_diff_density_max         0.83

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         7067
_refine_ls_number_restraints     2
_refine_ls_number_parameters     463
_oxford_refine_ls_R_factor_ref   0.0413
_refine_ls_wR_factor_ref         0.1010
_refine_ls_goodness_of_fit_ref   0.9369
_refine_ls_shift/su_max          0.0017660
_refine_ls_shift/su_mean         0.0000704

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7067
_refine_ls_R_factor_all          0.0413
_refine_ls_wR_factor_all         0.1010

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6862
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_gt          0.1008

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.186E+04 0.310E+04 0.191E+04 788. 177. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.90643(11) 0.44323(4) 0.89602(11) 0.0128 1.0000 Uani . . . . . .
C2 C 0.81816(13) 0.41567(5) 0.91401(13) 0.0144 1.0000 Uani . . . . . .
C3 C 0.77832(14) 0.37822(5) 0.82286(15) 0.0206 1.0000 Uani . . . . . .
C4 C 0.84516(15) 0.38310(5) 0.75293(14) 0.0204 1.0000 Uani . . . . . .
C5 C 0.92556(13) 0.42392(5) 0.79920(13) 0.0150 1.0000 Uani . . . . . .
C6 C 1.01059(13) 0.44080(5) 0.75075(13) 0.0148 1.0000 Uani . . . . . .
C7 C 1.08823(13) 0.48059(5) 0.79302(13) 0.0147 1.0000 Uani . . . . . .
N8 N 1.09118(11) 0.51040(4) 0.88496(11) 0.0133 1.0000 Uani . . . . . .
C9 C 1.18599(13) 0.54233(5) 0.90188(13) 0.0146 1.0000 Uani . . . . . .
C10 C 1.24271(14) 0.53293(5) 0.81589(14) 0.0189 1.0000 Uani . . . . . .
C11 C 1.18300(15) 0.49473(5) 0.74903(15) 0.0193 1.0000 Uani . . . . . .
C12 C 1.02527(13) 0.41229(5) 0.65117(13) 0.0155 1.0000 Uani . . . . . .
C13 C 1.08256(14) 0.36847(5) 0.68179(14) 0.0192 1.0000 Uani . . . . . .
C14 C 1.09970(15) 0.34154(5) 0.59169(14) 0.0199 1.0000 Uani . . . . . .
C15 C 1.05695(14) 0.35794(5) 0.46877(14) 0.0174 1.0000 Uani . . . . . .
C16 C 0.99869(15) 0.40148(5) 0.43727(14) 0.0206 1.0000 Uani . . . . . .
C17 C 0.98413(15) 0.42862(5) 0.52826(14) 0.0201 1.0000 Uani . . . . . .
C18 C 1.06836(14) 0.32956(5) 0.36813(14) 0.0189 1.0000 Uani . . . . . .
O19 O 1.15746(11) 0.29645(4) 0.41101(11) 0.0262 1.0000 Uani D . . . . .
O20 O 1.00263(11) 0.33667(4) 0.25679(10) 0.0266 1.0000 Uani . . . . . .
C21 C 1.22729(13) 0.57743(5) 0.99374(13) 0.0143 1.0000 Uani . . . . . .
C22 C 1.33297(13) 0.60914(5) 0.99895(13) 0.0156 1.0000 Uani . . . . . .
C23 C 1.30614(14) 0.65525(5) 0.95985(15) 0.0204 1.0000 Uani . . . . . .
C24 C 1.40514(14) 0.68597(5) 0.97572(15) 0.0211 1.0000 Uani . . . . . .
C25 C 1.53227(14) 0.67051(5) 1.02702(14) 0.0177 1.0000 Uani . . . . . .
C26 C 1.55921(14) 0.62406(6) 1.06058(16) 0.0235 1.0000 Uani . . . . . .
C27 C 1.46062(15) 0.59371(5) 1.04853(16) 0.0227 1.0000 Uani . . . . . .
C28 C 1.64061(14) 0.70323(5) 1.04889(14) 0.0209 1.0000 Uani . . . . . .
O29 O 1.60759(12) 0.74714(4) 1.04280(15) 0.0369 1.0000 Uani D . . . . .
O30 O 1.74886(11) 0.69022(4) 1.07026(13) 0.0311 1.0000 Uani . . . . . .
N51 N 0.84194(11) 0.54697(4) 0.89148(11) 0.0153 1.0000 Uani . . . . . .
C52 C 0.72135(14) 0.53488(5) 0.86804(15) 0.0215 1.0000 Uani . . . . . .
C53 C 0.61722(14) 0.56454(5) 0.81496(16) 0.0227 1.0000 Uani . . . . . .
C54 C 0.63627(14) 0.60943(5) 0.78170(14) 0.0176 1.0000 Uani . . . . . .
C55 C 0.76146(14) 0.62219(5) 0.80474(15) 0.0200 1.0000 Uani . . . . . .
C56 C 0.86041(14) 0.59018(5) 0.85935(14) 0.0188 1.0000 Uani . . . . . .
C57 C 0.52544(14) 0.64152(5) 0.72421(14) 0.0187 1.0000 Uani . . . . . .
C58 C 0.40141(15) 0.62404(6) 0.65263(16) 0.0249 1.0000 Uani . . . . . .
C59 C 0.29884(15) 0.65464(6) 0.60450(17) 0.0280 1.0000 Uani . . . . . .
N60 N 0.31200(13) 0.70034(5) 0.62416(14) 0.0261 1.0000 Uani . . . . . .
C61 C 0.43086(16) 0.71725(6) 0.69166(15) 0.0238 1.0000 Uani . . . . . .
C62 C 0.53954(15) 0.68953(5) 0.74195(14) 0.0209 1.0000 Uani . . . . . .
O101 O 0.81563(11) 0.75020(5) 0.76538(11) 0.0307 1.0000 Uani . . . . . .
S102 S 0.92531(4) 0.769777(15) 0.88153(4) 0.0293 1.0000 Uani . . . . . .
C103 C 0.99706(18) 0.72127(7) 0.98290(17) 0.0328 1.0000 Uani . . . . . .
C104 C 1.0521(2) 0.78189(8) 0.83579(19) 0.0422 1.0000 Uani . . . . . .
O111 O 0.4135(2) 0.49539(9) 0.6454(2) 0.0852 1.0000 Uani . . . . . .
C112 C 0.2772(3) 0.48266(14) 0.4318(3) 0.0831 1.0000 Uani . . . . . .
C113 C 0.3779(2) 0.46919(9) 0.5548(2) 0.0538 1.0000 Uani . . . . . .
C114 C 0.4136(4) 0.41882(14) 0.5718(4) 0.1013 1.0000 Uani . . . . . .
Ni1 Ni 1.0000 0.5000 1.0000 0.0108 1.0000 Uani S . . . . .
H31 H 0.7177 0.3533 0.8145 0.0260 1.0000 Uiso R . . . . .
H41 H 0.8417 0.3629 0.6866 0.0254 1.0000 Uiso R . . . . .
H101 H 1.3099 0.5504 0.8103 0.0236 1.0000 Uiso R . . . . .
H111 H 1.1996 0.4796 0.6833 0.0242 1.0000 Uiso R . . . . .
H131 H 1.1115 0.3577 0.7655 0.0240 1.0000 Uiso R . . . . .
H141 H 1.1403 0.3114 0.6155 0.0248 1.0000 Uiso R . . . . .
H161 H 0.9687 0.4129 0.3512 0.0248 1.0000 Uiso R . . . . .
H171 H 0.9455 0.4595 0.5063 0.0263 1.0000 Uiso R . . . . .
H231 H 1.2193 0.6665 0.9234 0.0270 1.0000 Uiso R . . . . .
H241 H 1.3860 0.7186 0.9515 0.0272 1.0000 Uiso R . . . . .
H261 H 1.6481 0.6139 1.0944 0.0290 1.0000 Uiso R . . . . .
H271 H 1.4819 0.5623 1.0787 0.0289 1.0000 Uiso R . . . . .
H521 H 0.7080 0.5037 0.8899 0.0262 1.0000 Uiso R . . . . .
H531 H 0.5319 0.5546 0.8046 0.0289 1.0000 Uiso R . . . . .
H551 H 0.7801 0.6526 0.7837 0.0246 1.0000 Uiso R . . . . .
H561 H 0.9475 0.5983 0.8763 0.0241 1.0000 Uiso R . . . . .
H581 H 0.3871 0.5923 0.6337 0.0316 1.0000 Uiso R . . . . .
H591 H 0.2144 0.6428 0.5564 0.0354 1.0000 Uiso R . . . . .
H611 H 0.4408 0.7494 0.7089 0.0285 1.0000 Uiso R . . . . .
H621 H 0.6217 0.7029 0.7875 0.0267 1.0000 Uiso R . . . . .
H1121 H 0.2996 0.4731 0.3659 0.1259 1.0000 Uiso R . . . . .
H1122 H 0.2633 0.5159 0.4239 0.1251 1.0000 Uiso R . . . . .
H1123 H 0.1954 0.4686 0.4170 0.1255 1.0000 Uiso R . . . . .
H1141 H 0.4123 0.4048 0.4943 0.1519 1.0000 Uiso R . . . . .
H1142 H 0.4981 0.4182 0.6366 0.1514 1.0000 Uiso R . . . . .
H1143 H 0.3573 0.4018 0.5985 0.1526 1.0000 Uiso R . . . . .
H1033 H 1.0180 0.6987 0.9357 0.0501 1.0000 Uiso R . . . . .
H1043 H 1.1282 0.7902 0.9088 0.0649 1.0000 Uiso R . . . . .
H1031 H 0.9338 0.7089 1.0118 0.0505 1.0000 Uiso R . . . . .
H191 H 1.163(2) 0.2825(8) 0.3509(19) 0.0421 1.0000 Uiso D . . . . .
H1032 H 1.0744 0.7314 1.0532 0.0503 1.0000 Uiso R . . . . .
H291 H 1.673(2) 0.7637(9) 1.060(3) 0.0579 1.0000 Uiso D . . . . .
H1042 H 1.0250 0.8071 0.7747 0.0649 1.0000 Uiso R . . . . .
H1041 H 1.0666 0.7541 0.7934 0.0650 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.61(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.3718(17) yes
N1 . C5 . 1.3657(18) yes
N1 . Ni1 . 2.0472(11) yes
C2 . C21 2_767 1.404(2) yes
C2 . C3 . 1.4484(19) yes
C3 . C4 . 1.350(2) yes
C3 . H31 . 0.975 no
C4 . C5 . 1.4478(19) yes
C4 . H41 . 0.960 no
C5 . C6 . 1.4098(19) yes
C6 . C7 . 1.4043(19) yes
C6 . C12 . 1.4963(18) yes
C7 . N8 . 1.3684(18) yes
C7 . C11 . 1.4478(19) yes
N8 . C9 . 1.3718(17) yes
N8 . Ni1 . 2.0547(11) yes
C9 . C10 . 1.4424(19) yes
C9 . C21 . 1.4043(19) yes
C10 . C11 . 1.354(2) yes
C10 . H101 . 0.945 no
C11 . H111 . 0.973 no
C12 . C13 . 1.396(2) yes
C12 . C17 . 1.395(2) yes
C13 . C14 . 1.392(2) yes
C13 . H131 . 0.945 no
C14 . C15 . 1.394(2) yes
C14 . H141 . 0.968 no
C15 . C16 . 1.393(2) yes
C15 . C18 . 1.4883(19) yes
C16 . C17 . 1.391(2) yes
C16 . H161 . 0.976 no
C17 . H171 . 0.977 no
C18 . O19 . 1.3289(19) yes
C18 . O20 . 1.2162(19) yes
O19 . H191 . 0.836(16) no
C21 . C22 . 1.4977(18) yes
C22 . C23 . 1.394(2) yes
C22 . C27 . 1.397(2) yes
C23 . C24 . 1.388(2) yes
C23 . H231 . 0.957 no
C24 . C25 . 1.392(2) yes
C24 . H241 . 0.978 no
C25 . C26 . 1.390(2) yes
C25 . C28 . 1.4913(19) yes
C26 . C27 . 1.387(2) yes
C26 . H261 . 0.968 no
C27 . H271 . 0.964 no
C28 . O29 . 1.312(2) yes
C28 . O30 . 1.216(2) yes
O29 . H291 . 0.841(17) no
N51 . C52 . 1.3365(19) yes
N51 . C56 . 1.3417(18) yes
N51 . Ni1 . 2.1827(12) yes
C52 . C53 . 1.381(2) yes
C52 . H521 . 0.962 no
C53 . C54 . 1.393(2) yes
C53 . H531 . 0.977 no
C54 . C55 . 1.393(2) yes
C54 . C57 . 1.4804(19) yes
C55 . C56 . 1.388(2) yes
C55 . H551 . 0.957 no
C56 . H561 . 0.961 no
C57 . C58 . 1.401(2) yes
C57 . C62 . 1.395(2) yes
C58 . C59 . 1.382(2) yes
C58 . H581 . 0.938 no
C59 . N60 . 1.332(2) yes
C59 . H591 . 0.952 no
N60 . C61 . 1.342(2) yes
C61 . C62 . 1.382(2) yes
C61 . H611 . 0.943 no
C62 . H621 . 0.944 no
O101 . S102 . 1.5152(12) yes
S102 . C103 . 1.790(2) yes
S102 . C104 . 1.787(2) yes
C103 . H1033 . 0.948 no
C103 . H1031 . 0.990 no
C103 . H1032 . 0.963 no
C104 . H1043 . 0.957 no
C104 . H1042 . 0.973 no
C104 . H1041 . 0.993 no
O111 . C113 . 1.223(3) yes
C112 . C113 . 1.465(4) yes
C112 . H1121 . 0.956 no
C112 . H1122 . 0.968 no
C112 . H1123 . 0.966 no
C113 . C114 . 1.496(4) yes
C114 . H1141 . 0.990 no
C114 . H1142 . 0.943 no
C114 . H1143 . 0.964 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 106.61(11) yes
C2 . N1 . Ni1 . 127.03(9) yes
C5 . N1 . Ni1 . 126.27(9) yes
C21 2_767 C2 . N1 . 125.45(12) yes
C21 2_767 C2 . C3 . 124.92(13) yes
N1 . C2 . C3 . 109.63(12) yes
C2 . C3 . C4 . 106.93(12) yes
C2 . C3 . H31 . 127.4 no
C4 . C3 . H31 . 125.6 no
C3 . C4 . C5 . 107.00(13) yes
C3 . C4 . H41 . 126.5 no
C5 . C4 . H41 . 126.5 no
C4 . C5 . N1 . 109.82(12) yes
C4 . C5 . C6 . 124.58(13) yes
N1 . C5 . C6 . 125.60(12) yes
C5 . C6 . C7 . 125.58(13) yes
C5 . C6 . C12 . 117.13(12) yes
C7 . C6 . C12 . 117.18(12) yes
C6 . C7 . N8 . 125.99(12) yes
C6 . C7 . C11 . 124.22(13) yes
N8 . C7 . C11 . 109.72(12) yes
C7 . N8 . C9 . 106.51(11) yes
C7 . N8 . Ni1 . 125.51(9) yes
C9 . N8 . Ni1 . 126.70(9) yes
N8 . C9 . C10 . 109.92(12) yes
N8 . C9 . C21 . 125.37(12) yes
C10 . C9 . C21 . 124.63(13) yes
C9 . C10 . C11 . 106.89(12) yes
C9 . C10 . H101 . 125.1 no
C11 . C10 . H101 . 128.0 no
C7 . C11 . C10 . 106.95(13) yes
C7 . C11 . H111 . 126.1 no
C10 . C11 . H111 . 126.9 no
C6 . C12 . C13 . 119.43(13) yes
C6 . C12 . C17 . 121.60(13) yes
C13 . C12 . C17 . 118.98(13) yes
C12 . C13 . C14 . 120.69(13) yes
C12 . C13 . H131 . 118.7 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 119.90(14) yes
C13 . C14 . H141 . 119.1 no
C15 . C14 . H141 . 121.0 no
C14 . C15 . C16 . 119.71(13) yes
C14 . C15 . C18 . 121.77(13) yes
C16 . C15 . C18 . 118.49(13) yes
C15 . C16 . C17 . 120.14(14) yes
C15 . C16 . H161 . 119.6 no
C17 . C16 . H161 . 120.2 no
C12 . C17 . C16 . 120.56(14) yes
C12 . C17 . H171 . 119.6 no
C16 . C17 . H171 . 119.8 no
C15 . C18 . O19 . 113.98(13) yes
C15 . C18 . O20 . 122.56(14) yes
O19 . C18 . O20 . 123.45(13) yes
C18 . O19 . H191 . 110.1(17) no
C9 . C21 . C2 2_767 125.50(12) yes
C9 . C21 . C22 . 118.06(12) yes
C2 2_767 C21 . C22 . 116.37(12) yes
C21 . C22 . C23 . 120.33(13) yes
C21 . C22 . C27 . 120.65(13) yes
C23 . C22 . C27 . 118.95(13) yes
C22 . C23 . C24 . 120.57(14) yes
C22 . C23 . H231 . 120.6 no
C24 . C23 . H231 . 118.8 no
C23 . C24 . C25 . 120.08(14) yes
C23 . C24 . H241 . 120.2 no
C25 . C24 . H241 . 119.7 no
C24 . C25 . C26 . 119.65(13) yes
C24 . C25 . C28 . 121.02(14) yes
C26 . C25 . C28 . 119.32(13) yes
C25 . C26 . C27 . 120.19(14) yes
C25 . C26 . H261 . 118.3 no
C27 . C26 . H261 . 121.5 no
C22 . C27 . C26 . 120.44(14) yes
C22 . C27 . H271 . 120.5 no
C26 . C27 . H271 . 119.0 no
C25 . C28 . O29 . 113.45(13) yes
C25 . C28 . O30 . 122.97(15) yes
O29 . C28 . O30 . 123.58(14) yes
C28 . O29 . H291 . 108.9(19) no
C52 . N51 . C56 . 117.21(12) yes
C52 . N51 . Ni1 . 119.21(10) yes
C56 . N51 . Ni1 . 123.09(9) yes
N51 . C52 . C53 . 123.51(14) yes
N51 . C52 . H521 . 117.2 no
C53 . C52 . H521 . 119.3 no
C52 . C53 . C54 . 119.34(13) yes
C52 . C53 . H531 . 120.2 no
C54 . C53 . H531 . 120.4 no
C53 . C54 . C55 . 117.54(13) yes
C53 . C54 . C57 . 119.92(13) yes
C55 . C54 . C57 . 122.55(13) yes
C54 . C55 . C56 . 119.16(13) yes
C54 . C55 . H551 . 121.1 no
C56 . C55 . H551 . 119.8 no
C55 . C56 . N51 . 123.24(13) yes
C55 . C56 . H561 . 120.5 no
N51 . C56 . H561 . 116.3 no
C54 . C57 . C58 . 120.29(14) yes
C54 . C57 . C62 . 121.78(14) yes
C58 . C57 . C62 . 117.90(14) yes
C57 . C58 . C59 . 119.09(15) yes
C57 . C58 . H581 . 121.4 no
C59 . C58 . H581 . 119.4 no
C58 . C59 . N60 . 122.94(16) yes
C58 . C59 . H591 . 119.2 no
N60 . C59 . H591 . 117.9 no
C59 . N60 . C61 . 118.12(14) yes
N60 . C61 . C62 . 123.16(15) yes
N60 . C61 . H611 . 118.8 no
C62 . C61 . H611 . 118.0 no
C57 . C62 . C61 . 118.76(15) yes
C57 . C62 . H621 . 120.8 no
C61 . C62 . H621 . 120.5 no
O101 . S102 . C103 . 106.17(8) yes
O101 . S102 . C104 . 105.72(8) yes
C103 . S102 . C104 . 98.63(10) yes
S102 . C103 . H1033 . 107.6 no
S102 . C103 . H1031 . 108.3 no
H1033 . C103 . H1031 . 111.1 no
S102 . C103 . H1032 . 109.1 no
H1033 . C103 . H1032 . 109.8 no
H1031 . C103 . H1032 . 110.9 no
S102 . C104 . H1043 . 109.1 no
S102 . C104 . H1042 . 108.9 no
H1043 . C104 . H1042 . 110.9 no
S102 . C104 . H1041 . 109.1 no
H1043 . C104 . H1041 . 111.5 no
H1042 . C104 . H1041 . 107.3 no
C113 . C112 . H1121 . 110.6 no
C113 . C112 . H1122 . 112.6 no
H1121 . C112 . H1122 . 107.2 no
C113 . C112 . H1123 . 111.3 no
H1121 . C112 . H1123 . 108.1 no
H1122 . C112 . H1123 . 106.8 no
C112 . C113 . O111 . 121.6(3) yes
C112 . C113 . C114 . 116.3(3) yes
O111 . C113 . C114 . 120.7(3) yes
C113 . C114 . H1141 . 112.1 no
C113 . C114 . H1142 . 104.7 no
H1141 . C114 . H1142 . 109.9 no
C113 . C114 . H1143 . 110.7 no
H1141 . C114 . H1143 . 110.1 no
H1142 . C114 . H1143 . 109.2 no
N51 . Ni1 . N51 2_767 179.995 yes
N51 . Ni1 . N8 . 93.16(4) yes
N51 2_767 Ni1 . N8 . 86.84(4) yes
N51 . Ni1 . N8 2_767 86.84(4) yes
N51 2_767 Ni1 . N8 2_767 93.16(4) yes
N8 . Ni1 . N8 2_767 179.994 yes
N51 . Ni1 . N1 2_767 87.01(4) yes
N51 2_767 Ni1 . N1 2_767 92.99(4) yes
N8 . Ni1 . N1 2_767 89.54(5) yes
N8 2_767 Ni1 . N1 2_767 90.46(5) yes
N51 . Ni1 . N1 . 92.99(4) yes
N51 2_767 Ni1 . N1 . 87.01(4) yes
N8 . Ni1 . N1 . 90.46(5) yes
N8 2_767 Ni1 . N1 . 89.54(5) yes
N1 2_767 Ni1 . N1 . 179.994 yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H131 . O30 2_867 149.00(5) 0.945 2.356 3.204(3) yes
C23 . H231 . O20 2_766 147.97(4) 0.957 2.524 3.373(3) yes
C52 . H521 . C9 2_767 131.74(5) 0.962 2.584 3.304(3) yes
C103 . H1033 . O20 2_766 153.38(5) 0.948 2.399 3.274(3) yes
C104 . H1043 . O19 4_756 168.19(6) 0.957 2.472 3.415(3) yes
C103 . H1031 . O30 1_455 169.77(5) 0.990 2.552 3.531(3) yes
O19 . H191 . O101 2_766 175(2) 0.836 1.762 2.596(3) yes
O29 . H291 . N60 3_665 170(3) 0.841 1.772 2.604(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 24/01/17 at 12: 7: 2
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL NI   (    1 ) 
CONT H    (  191 ,X'S) 
CONT H    (  291 ,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   ( 103,X'S) H   (1033,X'S) H   (1031,X'S) H   (1032,X'S) 
RIDE C   ( 104,X'S) H   (1043,X'S) H   (1042,X'S) H   (1041,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) H   (1122,X'S) H   (1123,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) H   (1142,X'S) H   (1143,X'S) 
END       
;

_iucr_refine_instructions_details_restraints 
;                                                                      
#
# Punched on 24/01/17 at 12: 7: 2
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 19) TO H(191) 
REST 0.040, 0.002 = H(191,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 29) TO H(291) 
REST 0.056, 0.002 = H(291,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4_bpy_DMSO_DCM
_database_code_depnum_ccdc_archive 'CCDC 1574950'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-15 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_DIFMN02_4_bpy_DMSO_DCM      
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: There is residual electron density around the dichloromethane solvent 
and there may be positional disorder of this molecule. This disorder
could not be sensibly modelled.
;
_vrf_PLAT029_4_bpy_DMSO_DCM      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.950 Note  
RESPONSE: Crystals were relatively small and weakly-diffracting, and so not all 
high angle reflections were observed. Nevertheless, the structure generally 
refines well, and the overall structure is clear.
;
_vrf_PLAT097_4_bpy_DMSO_DCM      
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.92 eA-3  
RESPONSE: There is residual electron density around the dichloromethane solvent 
and there may be positional disorder of this molecule. This disorder
could not be sensibly modelled.
;
_vrf_PLAT098_4_bpy_DMSO_DCM      
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -2.88 eA-3  
RESPONSE: There is residual electron density around the dichloromethane solvent 
and there may be positional disorder of this molecule. This disorder
could not be sensibly modelled.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
The asymmetric unit cell contains half of the compound as well as one
DMSO and one DCM solvate.

Crystals were relatively small and weakly-diffracting, and so not all high
angle reflections were observed. Nevertheless, the structure generally refines
well, and the overall structure is clear.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

There is residual electron density around the dichloromethane solvent, 
and there may be positional disorder of this molecule. This disorder
could not be sensibly modelled, and it was necessary to apply restraints to the
C-Cl bond lengths and the thermal and vibrational ellipsoid parameters of the 
dichloromethane molecule in order to achieve a sensible refinement.
;

_cell_length_a                   11.4326(6)
_cell_length_b                   29.0833(11)
_cell_length_c                   11.5789(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.102(7)
_cell_angle_gamma                90
_cell_volume                     3457.3(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ni -3.0029 0.5091 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

_chemical_formula_sum            'C37 H30 Cl2 N4 Ni0.5 O5 S1'
_chemical_formula_moiety         'C34 H22 N4 Ni0.5 O4, C2 H6 O S, C H2 Cl2'
_chemical_compound_source        synthesized
_chemical_formula_weight         743.00

_cell_measurement_reflns_used    4181
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      69.1
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1535.993
_exptl_absorpt_coefficient_mu    2.937

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            18635
_reflns_number_total             6003
_diffrn_reflns_av_R_equivalents  0.043

_diffrn_reflns_theta_min         4.516
_diffrn_reflns_theta_max         68.220
_diffrn_measured_fraction_theta_max 0.948

_diffrn_reflns_theta_full        67.348
_diffrn_measured_fraction_theta_full 0.950

_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -13
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              34
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.29
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -2.88
_refine_diff_density_max         2.92

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5975
_refine_ls_number_restraints     20
_refine_ls_number_parameters     454
_oxford_refine_ls_R_factor_ref   0.1062
_refine_ls_wR_factor_ref         0.1845
_refine_ls_goodness_of_fit_ref   0.9772
_refine_ls_shift/su_max          0.0001400
_refine_ls_shift/su_mean         0.0000121

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5975
_refine_ls_R_factor_all          0.1062
_refine_ls_wR_factor_all         0.1845

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4467
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_gt          0.1642

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.310E+04 0.468E+04 0.269E+04 994. 131. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.4108(4) 0.44240(14) 0.3971(4) 0.0188 1.0000 Uani . . . . . .
C2 C 0.3209(5) 0.41514(17) 0.4128(5) 0.0211 1.0000 Uani . . . . . .
C3 C 0.2833(6) 0.37769(19) 0.3208(6) 0.0292 1.0000 Uani . . . . . .
C4 C 0.3529(6) 0.38264(19) 0.2530(6) 0.0274 1.0000 Uani . . . . . .
C5 C 0.4317(5) 0.42334(17) 0.2997(5) 0.0208 1.0000 Uani . . . . . .
C6 C 0.5177(5) 0.43999(18) 0.2531(5) 0.0214 1.0000 Uani . . . . . .
C7 C 0.5961(5) 0.47964(18) 0.2969(5) 0.0208 1.0000 Uani . . . . . .
N8 N 0.5983(4) 0.50894(14) 0.3901(4) 0.0187 1.0000 Uani . . . . . .
C9 C 0.6905(5) 0.54145(17) 0.4064(5) 0.0198 1.0000 Uani . . . . . .
C10 C 0.7461(5) 0.53275(19) 0.3185(6) 0.0273 1.0000 Uani . . . . . .
C11 C 0.6892(5) 0.4948(2) 0.2523(5) 0.0257 1.0000 Uani . . . . . .
C12 C 0.5325(5) 0.41192(18) 0.1511(5) 0.0228 1.0000 Uani . . . . . .
C13 C 0.5887(5) 0.36823(19) 0.1815(5) 0.0246 1.0000 Uani . . . . . .
C14 C 0.6060(5) 0.34172(19) 0.0899(5) 0.0257 1.0000 Uani . . . . . .
C15 C 0.5622(5) 0.35855(19) -0.0350(6) 0.0262 1.0000 Uani . . . . . .
C16 C 0.5061(5) 0.4019(2) -0.0653(5) 0.0277 1.0000 Uani . . . . . .
C17 C 0.4920(5) 0.42855(19) 0.0268(5) 0.0258 1.0000 Uani . . . . . .
C18 C 0.5727(5) 0.33050(19) -0.1373(6) 0.0257 1.0000 Uani . . . . . .
O19 O 0.6631(4) 0.29782(15) -0.0926(4) 0.0342 1.0000 Uani D . . . . .
O20 O 0.5072(4) 0.33765(14) -0.2517(4) 0.0333 1.0000 Uani . . . . . .
C21 C 0.2722(5) 0.42247(18) 0.5032(5) 0.0227 1.0000 Uani . . . . . .
C22 C 0.1679(5) 0.38998(18) 0.4981(5) 0.0225 1.0000 Uani . . . . . .
C23 C 0.0408(5) 0.40486(19) 0.4572(6) 0.0269 1.0000 Uani . . . . . .
C24 C -0.0576(5) 0.37407(19) 0.4443(6) 0.0279 1.0000 Uani . . . . . .
C25 C -0.0288(5) 0.32791(19) 0.4699(5) 0.0239 1.0000 Uani . . . . . .
C26 C 0.0995(5) 0.31284(19) 0.5148(6) 0.0269 1.0000 Uani . . . . . .
C27 C 0.1963(5) 0.34394(19) 0.5297(5) 0.0253 1.0000 Uani . . . . . .
C28 C -0.1363(5) 0.29479(19) 0.4473(5) 0.0262 1.0000 Uani . . . . . .
O29 O -0.2447(4) 0.30643(14) 0.4282(4) 0.0370 1.0000 Uani . . . . . .
O30 O -0.1010(4) 0.25140(15) 0.4496(5) 0.0454 1.0000 Uani D . . . . .
N51 N 0.6630(4) 0.45610(15) 0.6251(4) 0.0237 1.0000 Uani . . . . . .
C52 C 0.7860(5) 0.4699(2) 0.6624(6) 0.0306 1.0000 Uani . . . . . .
C53 C 0.8914(6) 0.4412(2) 0.7156(6) 0.0337 1.0000 Uani . . . . . .
C54 C 0.8744(5) 0.39471(19) 0.7331(5) 0.0248 1.0000 Uani . . . . . .
C55 C 0.7470(5) 0.38069(18) 0.6990(6) 0.0280 1.0000 Uani . . . . . .
C56 C 0.6459(5) 0.41193(19) 0.6459(6) 0.0268 1.0000 Uani . . . . . .
C57 C 0.9865(5) 0.36240(19) 0.7859(5) 0.0262 1.0000 Uani . . . . . .
C58 C 1.1123(5) 0.3780(2) 0.8610(6) 0.0307 1.0000 Uani . . . . . .
C59 C 1.2137(6) 0.3472(2) 0.9006(6) 0.0326 1.0000 Uani . . . . . .
N60 N 1.1978(5) 0.30244(17) 0.8734(5) 0.0322 1.0000 Uani . . . . . .
C61 C 1.0768(6) 0.2871(2) 0.8037(6) 0.0306 1.0000 Uani . . . . . .
C62 C 0.9691(6) 0.31559(19) 0.7590(6) 0.0278 1.0000 Uani . . . . . .
O101 O 1.1938(4) 0.24817(15) 0.2318(4) 0.0369 1.0000 Uani . . . . . .
S102 S 1.08478(15) 0.26886(6) 0.11281(15) 0.0356 1.0000 Uani . . . . . .
C103 C 1.0070(7) 0.2219(2) 0.0076(6) 0.0386 1.0000 Uani . . . . . .
C104 C 0.9586(7) 0.2821(3) 0.1579(7) 0.0520 1.0000 Uani . . . . . .
C111 C 0.8254(10) 0.4367(3) 0.0121(12) 0.1458 1.0000 Uani D U . . . .
Cl112 Cl 0.9824(5) 0.42797(18) 0.1187(5) 0.2043 1.0000 Uani D U . . . .
Cl113 Cl 0.7844(3) 0.49451(11) -0.0252(3) 0.0960 1.0000 Uani D U . . . .
Ni1 Ni 0.5000 0.5000 0.5000 0.0182 1.0000 Uani S . . . . .
H31 H 0.2227 0.3546 0.3107 0.0363 1.0000 Uiso R . . . . .
H41 H 0.3494 0.3629 0.1878 0.0332 1.0000 Uiso R . . . . .
H101 H 0.8100 0.5503 0.3099 0.0325 1.0000 Uiso R . . . . .
H111 H 0.7061 0.4803 0.1890 0.0322 1.0000 Uiso R . . . . .
H131 H 0.6156 0.3567 0.2654 0.0305 1.0000 Uiso R . . . . .
H141 H 0.6459 0.3130 0.1125 0.0318 1.0000 Uiso R . . . . .
H161 H 0.4786 0.4127 -0.1493 0.0343 1.0000 Uiso R . . . . .
H171 H 0.4565 0.4583 0.0066 0.0322 1.0000 Uiso R . . . . .
H231 H 0.0233 0.4363 0.4391 0.0330 1.0000 Uiso R . . . . .
H241 H -0.1440 0.3846 0.4179 0.0342 1.0000 Uiso R . . . . .
H261 H 0.1200 0.2814 0.5351 0.0342 1.0000 Uiso R . . . . .
H271 H 0.2826 0.3338 0.5624 0.0323 1.0000 Uiso R . . . . .
H521 H 0.8008 0.5013 0.6516 0.0372 1.0000 Uiso R . . . . .
H531 H 0.9761 0.4529 0.7419 0.0412 1.0000 Uiso R . . . . .
H551 H 0.7297 0.3502 0.7122 0.0340 1.0000 Uiso R . . . . .
H561 H 0.5605 0.4017 0.6234 0.0332 1.0000 Uiso R . . . . .
H581 H 1.1267 0.4089 0.8837 0.0383 1.0000 Uiso R . . . . .
H591 H 1.2979 0.3580 0.9493 0.0415 1.0000 Uiso R . . . . .
H611 H 1.0657 0.2555 0.7856 0.0372 1.0000 Uiso R . . . . .
H621 H 0.8850 0.3038 0.7112 0.0341 1.0000 Uiso R . . . . .
H301 H -0.165(5) 0.235(2) 0.426(8) 0.0683 1.0000 Uiso D . . . . .
H191 H 0.671(7) 0.283(2) -0.150(5) 0.0526 1.0000 Uiso D . . . . .
H1041 H 0.8869 0.2952 0.0867 0.0656 1.0000 Uiso R . . . . .
H1042 H 0.9314 0.2547 0.1837 0.0656 1.0000 Uiso R . . . . .
H1043 H 0.9901 0.3033 0.2273 0.0656 1.0000 Uiso R . . . . .
H1031 H 0.9375 0.2331 -0.0689 0.0467 1.0000 Uiso R . . . . .
H1032 H 0.9738 0.2010 0.0491 0.0467 1.0000 Uiso R . . . . .
H1033 H 1.0684 0.2064 -0.0134 0.0467 1.0000 Uiso R . . . . .
H1111 H 0.8074 0.4203 -0.0648 0.1446 1.0000 Uiso R . . . . .
H1112 H 0.7722 0.4252 0.0496 0.1446 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.95(7)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.372(6) yes
N1 . C5 . 1.368(7) yes
N1 . Ni1 . 2.048(4) yes
C2 . C3 . 1.450(7) yes
C2 . C21 . 1.401(7) yes
C3 . C4 . 1.349(8) yes
C3 . H31 . 0.935 no
C4 . C5 . 1.441(7) yes
C4 . H41 . 0.935 no
C5 . C6 . 1.400(7) yes
C6 . C7 . 1.411(7) yes
C6 . C12 . 1.505(7) yes
C7 . N8 . 1.366(6) yes
C7 . C11 . 1.441(7) yes
N8 . C9 . 1.366(6) yes
N8 . Ni1 . 2.052(4) yes
C9 . C21 2_666 1.409(7) yes
C9 . C10 . 1.440(7) yes
C10 . C11 . 1.339(8) yes
C10 . H101 . 0.932 no
C11 . H111 . 0.935 no
C12 . C13 . 1.398(8) yes
C12 . C17 . 1.390(8) yes
C13 . C14 . 1.394(7) yes
C13 . H131 . 0.942 no
C14 . C15 . 1.395(8) yes
C14 . H141 . 0.933 no
C15 . C16 . 1.388(8) yes
C15 . C18 . 1.486(7) yes
C16 . C17 . 1.384(7) yes
C16 . H161 . 0.934 no
C17 . H171 . 0.940 no
C18 . O19 . 1.330(7) yes
C18 . O20 . 1.219(7) yes
O19 . H191 . 0.829(19) no
C21 . C22 . 1.502(7) yes
C22 . C23 . 1.384(8) yes
C22 . C27 . 1.388(8) yes
C23 . C24 . 1.394(7) yes
C23 . H231 . 0.940 no
C24 . C25 . 1.383(8) yes
C24 . H241 . 0.947 no
C25 . C26 . 1.394(8) yes
C25 . C28 . 1.491(7) yes
C26 . C27 . 1.380(7) yes
C26 . H261 . 0.948 no
C27 . H271 . 0.935 no
C28 . O29 . 1.208(7) yes
C28 . O30 . 1.322(7) yes
O30 . H301 . 0.82(2) no
N51 . C52 . 1.339(7) yes
N51 . C56 . 1.337(7) yes
N51 . Ni1 . 2.197(4) yes
C52 . C53 . 1.368(8) yes
C52 . H521 . 0.947 no
C53 . C54 . 1.395(8) yes
C53 . H531 . 0.941 no
C54 . C55 . 1.392(8) yes
C54 . C57 . 1.486(7) yes
C55 . C56 . 1.384(8) yes
C55 . H551 . 0.936 no
C56 . H561 . 0.941 no
C57 . C58 . 1.390(8) yes
C57 . C62 . 1.391(8) yes
C58 . C59 . 1.374(8) yes
C58 . H581 . 0.931 no
C59 . N60 . 1.334(8) yes
C59 . H591 . 0.930 no
N60 . C61 . 1.336(8) yes
C61 . C62 . 1.382(8) yes
C61 . H611 . 0.939 no
C62 . H621 . 0.939 no
O101 . S102 . 1.517(4) yes
S102 . C103 . 1.786(7) yes
S102 . C104 . 1.779(7) yes
C103 . H1031 . 0.950 no
C103 . H1032 . 0.950 no
C103 . H1033 . 0.950 no
C104 . H1041 . 0.950 no
C104 . H1042 . 0.950 no
C104 . H1043 . 0.950 no
C111 . Cl112 . 1.691(8) yes
C111 . Cl113 . 1.748(8) yes
C111 . H1111 . 0.950 no
C111 . H1112 . 0.950 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 106.7(4) yes
C2 . N1 . Ni1 . 127.3(3) yes
C5 . N1 . Ni1 . 126.0(3) yes
N1 . C2 . C3 . 109.5(4) yes
N1 . C2 . C21 . 125.3(5) yes
C3 . C2 . C21 . 125.2(5) yes
C2 . C3 . C4 . 106.7(5) yes
C2 . C3 . H31 . 126.5 no
C4 . C3 . H31 . 126.8 no
C3 . C4 . C5 . 107.5(5) yes
C3 . C4 . H41 . 125.3 no
C5 . C4 . H41 . 127.2 no
C4 . C5 . N1 . 109.6(4) yes
C4 . C5 . C6 . 124.6(5) yes
N1 . C5 . C6 . 125.8(5) yes
C5 . C6 . C7 . 125.9(5) yes
C5 . C6 . C12 . 117.1(5) yes
C7 . C6 . C12 . 116.9(4) yes
C6 . C7 . N8 . 125.6(4) yes
C6 . C7 . C11 . 125.0(5) yes
N8 . C7 . C11 . 109.4(4) yes
C7 . N8 . C9 . 106.6(4) yes
C7 . N8 . Ni1 . 125.9(3) yes
C9 . N8 . Ni1 . 127.0(3) yes
C21 2_666 C9 . N8 . 125.6(5) yes
C21 2_666 C9 . C10 . 124.9(5) yes
N8 . C9 . C10 . 109.5(4) yes
C9 . C10 . C11 . 107.2(5) yes
C9 . C10 . H101 . 126.2 no
C11 . C10 . H101 . 126.6 no
C7 . C11 . C10 . 107.2(5) yes
C7 . C11 . H111 . 125.7 no
C10 . C11 . H111 . 127.0 no
C6 . C12 . C13 . 119.6(5) yes
C6 . C12 . C17 . 121.5(5) yes
C13 . C12 . C17 . 118.9(5) yes
C12 . C13 . C14 . 121.0(5) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 119.8 no
C13 . C14 . C15 . 119.3(5) yes
C13 . C14 . H141 . 119.8 no
C15 . C14 . H141 . 120.9 no
C14 . C15 . C16 . 119.7(5) yes
C14 . C15 . C18 . 121.0(5) yes
C16 . C15 . C18 . 119.2(5) yes
C15 . C16 . C17 . 120.7(5) yes
C15 . C16 . H161 . 118.3 no
C17 . C16 . H161 . 121.0 no
C12 . C17 . C16 . 120.3(5) yes
C12 . C17 . H171 . 119.3 no
C16 . C17 . H171 . 120.4 no
C15 . C18 . O19 . 113.8(5) yes
C15 . C18 . O20 . 123.1(5) yes
O19 . C18 . O20 . 123.1(5) yes
C18 . O19 . H191 . 113(5) no
C9 2_666 C21 . C2 . 125.3(5) yes
C9 2_666 C21 . C22 . 118.2(5) yes
C2 . C21 . C22 . 116.4(5) yes
C21 . C22 . C23 . 120.8(5) yes
C21 . C22 . C27 . 120.5(5) yes
C23 . C22 . C27 . 118.7(5) yes
C22 . C23 . C24 . 120.8(5) yes
C22 . C23 . H231 . 118.0 no
C24 . C23 . H231 . 121.2 no
C23 . C24 . C25 . 119.7(5) yes
C23 . C24 . H241 . 120.3 no
C25 . C24 . H241 . 120.0 no
C24 . C25 . C26 . 119.8(5) yes
C24 . C25 . C28 . 119.3(5) yes
C26 . C25 . C28 . 120.9(5) yes
C25 . C26 . C27 . 119.7(5) yes
C25 . C26 . H261 . 120.0 no
C27 . C26 . H261 . 120.3 no
C22 . C27 . C26 . 121.2(5) yes
C22 . C27 . H271 . 119.5 no
C26 . C27 . H271 . 119.3 no
C25 . C28 . O29 . 123.4(5) yes
C25 . C28 . O30 . 113.1(5) yes
O29 . C28 . O30 . 123.4(5) yes
C28 . O30 . H301 . 110(6) no
C52 . N51 . C56 . 116.5(5) yes
C52 . N51 . Ni1 . 120.3(4) yes
C56 . N51 . Ni1 . 121.9(4) yes
N51 . C52 . C53 . 123.6(5) yes
N51 . C52 . H521 . 118.1 no
C53 . C52 . H521 . 118.3 no
C52 . C53 . C54 . 120.4(5) yes
C52 . C53 . H531 . 120.3 no
C54 . C53 . H531 . 119.3 no
C53 . C54 . C55 . 116.0(5) yes
C53 . C54 . C57 . 121.6(5) yes
C55 . C54 . C57 . 122.4(5) yes
C54 . C55 . C56 . 119.9(5) yes
C54 . C55 . H551 . 120.1 no
C56 . C55 . H551 . 120.0 no
C55 . C56 . N51 . 123.4(5) yes
C55 . C56 . H561 . 118.5 no
N51 . C56 . H561 . 118.1 no
C54 . C57 . C58 . 121.2(5) yes
C54 . C57 . C62 . 121.0(5) yes
C58 . C57 . C62 . 117.8(5) yes
C57 . C58 . C59 . 119.0(6) yes
C57 . C58 . H581 . 119.9 no
C59 . C58 . H581 . 121.1 no
C58 . C59 . N60 . 123.4(6) yes
C58 . C59 . H591 . 118.6 no
N60 . C59 . H591 . 118.1 no
C59 . N60 . C61 . 117.8(5) yes
N60 . C61 . C62 . 122.8(6) yes
N60 . C61 . H611 . 117.7 no
C62 . C61 . H611 . 119.6 no
C57 . C62 . C61 . 119.2(6) yes
C57 . C62 . H621 . 119.9 no
C61 . C62 . H621 . 120.9 no
O101 . S102 . C103 . 106.2(3) yes
O101 . S102 . C104 . 105.5(3) yes
C103 . S102 . C104 . 98.1(3) yes
S102 . C103 . H1031 . 109.5 no
S102 . C103 . H1032 . 109.4 no
H1031 . C103 . H1032 . 109.5 no
S102 . C103 . H1033 . 109.5 no
H1031 . C103 . H1033 . 109.5 no
H1032 . C103 . H1033 . 109.5 no
S102 . C104 . H1041 . 109.6 no
S102 . C104 . H1042 . 109.3 no
H1041 . C104 . H1042 . 109.5 no
S102 . C104 . H1043 . 109.6 no
H1041 . C104 . H1043 . 109.5 no
H1042 . C104 . H1043 . 109.5 no
Cl112 . C111 . Cl113 . 114.1(6) yes
Cl112 . C111 . H1111 . 109.3 no
Cl113 . C111 . H1111 . 109.2 no
Cl112 . C111 . H1112 . 107.5 no
Cl113 . C111 . H1112 . 107.2 no
H1111 . C111 . H1112 . 109.5 no
N51 . Ni1 . N51 2_666 179.995 yes
N51 . Ni1 . N8 2_666 93.13(16) yes
N51 2_666 Ni1 . N8 2_666 86.87(16) yes
N51 . Ni1 . N8 . 86.87(16) yes
N51 2_666 Ni1 . N8 . 93.12(16) yes
N8 2_666 Ni1 . N8 . 179.994 yes
N51 . Ni1 . N1 . 88.21(17) yes
N51 2_666 Ni1 . N1 . 91.79(17) yes
N8 2_666 Ni1 . N1 . 89.38(16) yes
N8 . Ni1 . N1 . 90.62(16) yes
N51 . Ni1 . N1 2_666 91.79(17) yes
N51 2_666 Ni1 . N1 2_666 88.21(17) yes
N8 2_666 Ni1 . N1 2_666 90.62(16) yes
N8 . Ni1 . N1 2_666 89.38(16) yes
N1 . Ni1 . N1 2_666 179.994 yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H131 . O29 1_655 147.28(16) 0.942 2.365 3.199(9) yes
C27 . H271 . O20 1_556 145.79(15) 0.935 2.525 3.340(9) yes
C56 . H561 . O20 1_556 122.94(15) 0.941 2.590 3.200(9) yes
O30 . H301 . N60 3_354 178(9) 0.820 1.775 2.595(9) yes
O19 . H191 . O101 3_454 177(8) 0.829 1.756 2.584(9) yes
C104 . H1041 . O19 . 156.1(2) 0.950 2.488 3.378(9) yes
C103 . H1032 . O20 3_555 147.24(18) 0.950 2.441 3.281(9) yes
C103 . H1033 . O29 3_654 160.28(17) 0.950 2.536 3.446(9) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 22/02/17 at 16:34:55
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL NI   (    1 ) 
CONT H    (  301 ,X'S)  UNTIL H    (  191 ) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) H   (1032,X'S) H   (1033,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) H   (1042,X'S) H   (1043,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) H   (1112,X'S) 
END     
;

_iucr_refine_instructions_details_restraints 
;                                                                      
#
# Punched on 22/02/17 at 16:34:55
#
#LIST     16                                                                    
DIST 1.77, 0.01 = C(111) TO CL(112), C(111) TO CL(113) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 19) TO H(191) 
REST 0.051, 0.002 = H(191,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 30) TO H(301) 
REST 0.068, 0.002 = H(301,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = C(111) TO CL(112) 
VIBR .0, 0.00200 = C(111) TO CL(113) 
VIBR .0, 0.00500 = CL(113) TO CL(112) 
VIBR .0, 0.00500 = CL(112) TO CL(113) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = C(111) TO CL(112) 
U(IJ) .0, 0.04000 = C(111) TO CL(113) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
